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Yuan Zhao et al.
1615 cmÀ1
;
1H NMR (400 MHz, CD3OD): d=7.63 (t, J=
113.2, 88.8, 78.8, 60.3, 58.2, 39.8, 27.5, 13.1; HR-MS (ESI-mi-
croTOF-QII): m/z=466.1630 [M+Na]+, calcd. for
C24H26FNNaO6: 466.1636.
8.2 Hz, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.43 (dd, J=8.2,
1.5 Hz, 2H), 7.24–7.32 (m, 3H), 7.13–7.19 (m, 2H), 7.08 (t,
J=7.4 Hz, 1H), 5.13 (d, J=10.0 Hz, 1H), 3.78–3.89 (m,
2H), 3.12 (d, J=16.1 Hz,1H), 2.60 (d, J=16.1 Hz, 1H), 1.31
(s, 9H), 0.90 (t, J=7.1 Hz, 3H); 13C NMR (100 MHz, ace-
tone-d6): d=200.7, 172.0, 167.7, 154.7, 137.6, 137.3, 128.6,
128.1, 128.0, 123.2, 123.0, 121.8, 113.2, 89.0, 78.7, 60.3, 60.0,
39.9, 27.5, 13.1; HR-MS (MALDI-TOF): m/z=464.1470
[M+K]+, calcd. for C24H27NKO6: 464.1475.
Ethyl
methoxyphenyl)methyl]benzofuran-3-one-2-acetate
yield: 195 mg (84%); mp 135–1368C; IR: v=3454, 1731,
1713, 1609 cmÀ1 1H NMR (400 MHz, CD3OD): d=7.38–
(2S*,1’R*)-2-[(tert-butoxycarbonylamino)(ortho-
(10f):
;
7.43 (m, 2H), 7.24 (d, J=7.2 Hz, 1H), 7.06 (t, J=7.5 Hz,
1H), 6.86–6.90 (m, 2H), 6.70–6.80 (m, 2H), 5.49 (d, J=
7.6 Hz, 1H), 3.64 (s, 3H), 3.54–3.60 (m, 2H), 2.94 (d, J=
16.4 Hz,1H), 2.32 (d, J=15.9 Hz, 1H), 1.07 (s, 9H), 0.65 (t,
J=7.1 Hz, 3H); 13C NMR (100 MHz, acetone-d6): d=201.0,
172.6, 168.8, 157.9, 155.5, 137.8, 130.4, 130.1, 126.9, 124.2,
124.0, 122.5, 121.5, 114.0, 111.8, 90.4, 79.4, 61.1, 56.0, 39.9,
30.6, 28.4, 14.0; HR-MS (ESI-microTOF-QII): m/z=
478.1855 [M+Na]+, calcd. for C25H29NNaO7: 478.1836.
Ethyl (2S*,1’R*)-2-[(tert-butoxycarbonylamino)(meta-me-
Ethyl (2S*,1’R*)-2-[(tert-butoxycarbonylamino)(para-me-
thoxyphenyl)methyl]benzofuran-3-one-2-acetate
yield: 202 mg (83%); mp 122–1238C; IR: v=3365, 1731,
1694, 1612 cmÀ1 1H NMR (400 MHz, acetone-d6): d=7.49
(10b):
;
(t, J=7.6 Hz, 1H), 7.41 (d, J=7.4 Hz, 1H), 7.34 (d, J=
8.2 Hz, 2H), 6.95 (d, J=6.8 Hz, 1H), 6.94 (t, J=6.4 Hz,
1H), 6.73 (d, J=8.0 Hz, 2H), 6.43 (d, J=9.3 Hz, 1H), 4.99
(d, J=10.2 Hz, 1H), 3.65–3.74 (m, 2H), 3.63 (s, 3H), 3.03
(d, J=16.2 Hz, 1H), 2.53 (d, J=16.2 Hz, 1H), 1.13 (s, 9H),
0.76 (t, J=7.1 Hz, 3H); 13C NMR (100 MHz, acetone-d6):
d=201.6, 172.8, 168.6, 160.4, 155.5, 138.1, 130.6, 124.0, 123.9,
122.6, 114.3, 114.0, 90.2, 79.5, 61.1, 59.3, 55.5, 40.8, 28.4,
14.0; HR-MS (ESI-microTOF-QII): m/z=478.1851 [M+
Na]+, calcd. for C25H29NNaO7: 478.1836.
thoxyphenyl)methyl]benzofuran-3-one-2-acetate
(10g):
yield: 168 mg (74%); mp 109–1108C; IR: v=3443, 1747,
1
1723, 1606 cmÀ1; H NMR (400 MHz, CD3OD): d=7.56 (t,
J=7.5 Hz, 1H), 7.49 (d, J=7.6 Hz, 1H), 7.13 (t, J=7.9 Hz,
1H), 7.08 (d, J=8.4 Hz, 1H), 7.01 (t, J=7.4 Hz, 1H), 6.94
(s, 1H), 6.91 (d, J=7.6 Hz, 1H), 6.75 (d, J=8.0 Hz, 1H),
5.02 (d, J=10.4 Hz, 1H), 3.73–3.81 (m, 2H), 3.71 (s, 3H),
3.03 (d, J=16.1 Hz, 1H), 2.54 (d, J=16.1 Hz, 1H), 1.23 (s,
9H), 0.82 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, acetone-
d6): d=200.6, 172.0, 167.7, 159.7, 154.7, 139.2, 137.2, 129.1,
123.2, 123.0, 121.7, 120.8, 114.2, 113.6, 113.2, 89.1, 78.6, 60.3,
59.0, 54.7, 39.9, 27.5, 13.1; HR-MS (ESI-microTOF-QII):
m/z=478.1839 [M+Na]+, calcd. for C25H29NNaO7: 478.1836.
Ethyl
(2S*,1’R*)-2-[(tert-butoxycarbonylamino)(para-
(10c):
methylphenyl)methyl]benzofuran-3-one-2-acetate
yield: 174 mg (78%); mp 102–1038C; IR: v=3383, 1745,
1713, 1613 cmÀ1; H NMR (400 MHz, CD3OD): d=7.64 (t,
1
J=7.5 Hz, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.31 (d, J=8.0 Hz,
2H), 7.07–7.16 (m, 5H), 5.07 (d, J=10.1 Hz, 1H), 3.77–3.88
(m, 2H), 3.09 (d, J=16.1 Hz,1H), 2.58 (d, J=16.1 Hz, 1H),
2.30 (s, 3H), 1.30 (s, 9H), 0.90 (t, J=7.1 Hz, 3H); 13C NMR
(100 MHz, acetone-d6): d=200.7, 172.0, 167.7, 154.6, 137.5,
137.2, 134.7, 128.7, 128.5, 123.2, 123.0, 121.7, 113.2, 89.1,
78.6, 60.2, 58.7, 39.9, 27.5, 20.2, 13.1; HR-MS (ESI-micro-
Ethyl
(2S*,1’R*)-2-[(tert-butoxycarbonylamino)-
AHCTUNGTREG(NNNU phenyl)methyl]-5-methoxybenzofuran-3-one-2-acetate
(10h): yield: 197 mg (86%); mp 138–1398C; IR: v=3448,
1
3368, 1736, 1721, 1709 cmÀ1; H NMR (500 MHz, CD3OD):
d=7.32 (d, J=6.6 Hz, 2H), 7.18–7.21 (m, 3H), 7.14 (dd, J=
9.0, 2.7 Hz, 1H), 7.07 (d, J=9.9 Hz, 1H), 6.96 (d, J=9.0 Hz,
1H), 6.92 (d, J=9.0 Hz, 1H), 5.00 (d, J=9.9 Hz, 1H), 3.70–
3.78 (m, 2H), 3.68 (s, 3H), 2.99 (d, J=16.0 Hz,1H), 2.47 (d,
J=16.0 Hz, 1H), 1.22 (s, 9H), 0.82 (t, J=7.1 Hz, 3H);
13C NMR (100 MHz, acetone-d6): d=201.7, 168.6, 168.0,
155.9, 155.6, 138.6, 129.4, 128.9, 128.8, 127.3, 123.8, 114.9,
104.7, 90,4, 79.6, 61.1, 59,9, 56.3, 40.9, 28.4, 14.0; HR-MS
(ESI-microTOF-QII): m/z=478.1840 [M+Na]+, calcd. for
C25H29NNaO7: 478.1836.
TOF-QII):
C25H29NNaO6: 462.1887.
m/z=462.1881
[M+Na]+,
calcd.
for
Ethyl (2S*,1’R*)-2-[(tert-butoxycarbonylamino)(para-bro-
mophenyl)methyl]benzofuran-3-one-2-acetate (10d): yield:
183 mg (65%); mp 113–1148C; IR: v=3360, 1738, 1717,
1615 cmÀ1; H NMR (400 MHz, acetone-d6): d=7.65 (t, J=
1
7.4 Hz, 1H), 7.50–7.57 (m, 5H), 7.10 (t, J=7.2 Hz, 1H), 7.09
(d, J=7.7 Hz, 1H), 6.73 (d, J=9.9 Hz, 1H), 5.19 (d, J=
10.2 Hz, 1H), 3.77–3.89 (m, 2H), 3.22 (d, J=16.3 Hz,1H),
2.69 (d, J=16.3 Hz, 1H), 1.28 (s, 9H), 0.91 (t, J=7.1 Hz,
3H); 13C NMR (100 MHz, acetone-d6): d=200.4, 171.9,
167.6, 154.7, 137.4, 137.1, 131.1, 130.7, 123.2, 122.8, 121.9,
121.6, 113.2, 88.7, 78.9, 60.3, 58.3, 39.8, 27.5, 13.1; HR-MS
(ESI-microTOF-QII): m/z=526.0812 [M+Na]+, calcd. for
C24H26BrNNaO6: 526.0836.
Ethyl
(phenyl)methyl]-7-methoxybenzofuran-3-one-2-acetate (10i):
yield: 201 mg (86%); mp 142–1438C; IR: v=3455, 1742,
1713 cmÀ1 1H NMR (400 MHz, CD3OD): d=7.32 (d, J=
(2S*,1’R*)-2-[(tert-butoxycarbonylamino)-
AHCTUNGTRENNUNG
;
6.7 Hz, 2H), 7.14–7.20 (m, 3H), 7.11 (d, J=7.9 Hz, 1H),
7.07 (d, J=10.6 Hz, 1H), 7.01 (d, J=7.6 Hz, 1H), 6.70 (t,
J=7.8 Hz, 1H), 5.02 (d, J=9.8 Hz, 1H), 3.84 (s, 3H), 3.70–
3.79 (m, 2H), 3.05 (d, J=16.2 Hz,1H), 2.56 (d, J=16.2 Hz,
1H), 1.22 (s, 9H), 0.81 (t, J=7.1 Hz, 3H); 13C NMR
(100 MHz, acetone-d6): d=201.7, 168.6, 162.9, 155.6, 147.3,
138.3, 129.3, 128.9, 128.8, 125.1, 123.2, 120.0, 115.2, 90.0,
79.6, 61.2, 59.8, 56.7, 40.7, 28.4, 14.0; HR-MS (ESI-micro-
Ethyl (2S*,1’R*)-2-[(tert-butoxycarbonylamino)(para-flu-
orophenyl)methyl]benzofuran-3-one-2-acetate (10e): yield:
189 mg (77%); mp 112–1138C; IR: v=3355, 1740, 1720,
1615 cmÀ1 1H NMR (400 MHz, CD3OD): d=7.65 (t, J=
;
8.3 Hz, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.46 (d, J=8.7 Hz,
1H), 7.45 (d, J=8.6 Hz, 1H), 7.20 (d, J=9.8 Hz, 1H), 7.14
(d, J=8.4 Hz, 1H), 7.45 (t, J=7.4 Hz, 1H), 6.99–7.03 (m,
2H), 5.14 (d, J=10.0 Hz, 1H), 3.81–3.88 (m, 2H), 3.14 (d,
J=16.1 Hz,1H), 2.63 (d, J=16.1 Hz, 1H), 1.32 (s, 9H), 0.91
(t, J=7.2 Hz, 3H); 13C NMR (100 MHz, acetone-d6): d=
200.6, 171.9, 167.7, 162.4 (d, J=243 Hz), 154.7, 137.4, 133.8,
130.6 (d, J=8 Hz), 123.2, 122.9, 121.8, 114.8 (d, J=21 Hz),
TOF-QII):
C25H29NNaO7: 478.1836.
Ethyl (2S*,1’R*)-2-[(tert-butoxycarbonylamino)-
(phenyl)methyl]-5-methylbenzofuran-3-one-2-acetate (10j):
m/z=478.1835
[M+Na]+,
calcd.
for
AHCTUNGTRENNUNG
yield: 172 mg (76%); mp 114–1158C; IR: v=3416, 1737,
1
1718, 1698 cmÀ1; H NMR (400 MHz, CD3OD): d=7.47 (d,
2586
ꢁ 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2014, 356, 2580 – 2590