The Journal of Organic Chemistry
Page 6 of 9
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1H), 3.02 (dd, J = 16.0, 6.8 Hz, 1H), 1.33 (d, J = 6.8 Hz, 3H),
0.75(s, 9H); 13C NMR (100 MHz, CDCl3, ppm) δ 171.9, 154.7,
145.7, 128.4, 127.1, 126.3, 65.2, 60.8, 42.9, 36.3, 35.5, 25.4,
22.3; HRMS (ESIꢀTOF) m/z: [M
C17H23NNaO3 312.1576; Found 312.1575.
leum ether/ethyl acetate (6:1). H NMR (400 MHz, CDCl3,
ppm) δ 7.54 (d, J = 8.0 Hz, 2H), 7.41 (d, J = 8.0 Hz, 2H), 4.37
(d, J = 1.6 Hz, 1H), 4.25 (m, 2H), 3.58 (dd, J = 16.0, 8.0 Hz,
1H), 3.48 (m, 1H), 3.02 (dd, J = 16.0, 6.4 Hz, 1H), 1.35 (d, J
= 6.8 Hz, 3H), 0.72(s, 9H); 13C NMR (100 MHz, CDCl3, ppm)
δ 171.5, 154.7, 149.8, 128.7 (q, J = 32.1 Hz), 127.5, 127.1 (q,
J = 270.1 Hz), 125.4 (q, J = 3.6 Hz), 65.2, 60.8, 42.6, 36.3,
35.5, 25.3, 22.1; HRMS (ESIꢀTOF) m/z: [M + H]+ Calcd for
C18H22F3NO3 358.1630; Found 358.1626.
+
Na]+ Calcd for
(S)-4-(tert-butyl)-3-((S)-3-phenylbutanoyl)oxazolidin-2-
one (3’a, 2 mg, yield 2%): Yellow solid. Eluent: petroleum
ether/ethyl acetate (10:1). 1H NMR (400 MHz, CDCl3, ppm) δ
7.28 (m, 4H), 7.19 (m, 1H), 4.31 (dd, J = 7.6, 1.6 Hz, 1H),
4.20 (dd, J = 9.2, 1.6Hz, 1H), 4.03 (dd, J = 9.2, 7.6Hz, 1H),
3.39(m, 2H), 3.02 (m, 1H), 1.34 (d, J = 6.8Hz, 3H), 0.88(s,
9H).
(S)-4-(tert-butyl)-3-((R)-3-(o-tolyl)butanoyl)oxazolidin-
2-one (3b, 109 mg, yield 72%): White solid, mp 55ꢀ56 °C.
Eluent: petroleum ether/ethyl acetate (7:1). 1H NMR (400
MHz, CDCl3, ppm) δ 7.27 (d, J = 9.6 Hz, 1H), 7.16 (7, J = 7.2
Hz, 1H), 7.07(m, 2H), 4.38 (d, J = 1.6 Hz, 1H), 4.22 (m, 2H),
3.68 (m, 1H), 3.57 (dd, J = 16.0, 7.6 Hz, 1H), 3.04 (dd, J =
16.0, 6.8 Hz, 1H), 2.38(s, 3H), 1.28 (d, J = 6.8 Hz, 3H), 0.72(s,
9H); 13C NMR (100 MHz, CDCl3, ppm) δ 172.2, 154.7, 144.0,
135.6, 130.4, 126.3, 126.0, 125.3, 65.1, 60.8, 42.0, 35.6, 31.3,
25.4, 21.9, 19.5; HRMS (ESIꢀTOF) m/z: [M + H]+ Calcd for
C18H25NO3 304.1913; Found 304.1910.
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(S)-4-(tert-butyl)-3-((R)-3-(2-
chlorophenyl)butanoyl)oxazolidin-2-one (3i, 115 mg, yield
71%): White solid, mp 89ꢀ90 °C. Eluent: petroleum ether/ethyl
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acetate (6:1). H NMR (400 MHz, CDCl3, ppm) δ 7.34 (m,
2H), 7.22 (m, 1H), 7.12 (m, 1H), 4.39 (dd, J = 7.6, 2.0 Hz,
1H), 4.23 (m, 2H), 3.92 (m, 1H), 3.42 (dd, J = 16.8, 6.8 Hz,
1H), 3.21 (dd, J = 16.8, 7.2 Hz, 1H), 1.32 (d, J = 7.2 Hz, 3H),
0.79(s, 9H); 13C NMR (100 MHz, CDCl3, ppm) δ 171.5, 154.7,
142.9, 133.7, 129.7, 127.4, 127.2, 127.1, 65.3, 60.9, 41.8, 35.7,
32.1, 25.5, 21.0; HRMS (ESI) m/z calcd for C17H23ClNO3
[M + H]+ 324.1366, found 324.1365.
(S)-4-(tert-butyl)-3-((R)-3-(3-
chlorophenyl)butanoyl)oxazolidin-2-one (3j, 122 mg, yield
75%): Yellow oil. Eluent: petroleum ether/ethyl acetate (6:1).
1H NMR (400 MHz, CDCl3, ppm) δ 7.27 (s, 1H), 7.17 (m, 3H),
4.38 (dd, J = 7.6, 2.0 Hz, 1H), 4.25 (m, 2H), 3.53 (dd, J =
16.0, 7.6 Hz, 1H), 3.39 (m, 1H), 2.98 (dd, J = 16.4, 6.8 Hz,
1H), 1.32 (d, J = 6.8 Hz, 3H), 0.76(s, 9H); 13C NMR (100
MHz, CDCl3, ppm) δ 171.6, 154.6, 147.8, 134.2, 129.7, 127.3,
126.5, 125.3, 65.2, 60.8, 42.7, 36.1, 35.6, 25.4, 22.1; HRMS
(ESIꢀTOF) m/z: [M + H]+ Calcd for C17H23NO3Cl 324.1366;
Found 324.1365.
(S)-4-(tert-butyl)-3-((R)-3-(m-tolyl)butanoyl)oxazolidin-
2-one (3c, 110 mg, yield 73%): Yellow oil. Eluent: petroleum
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ether/ethyl acetate (7:1). H NMR (400 MHz, CDCl3, ppm) δ
7.17 (t, J = 7.6 Hz, 1H), 7.08 (m, 2H), 6.98 (t, J = 7.2 Hz, 1H),
4.39 (d, J = 2.0 Hz, 1H), 4.20 (m, 2H), 3.54 (dd, J = 16, 7.6
Hz, 1H), 3.37 (m, 1H), 3.01 (dd, J = 16.0, 7.2 Hz, 1H), 2.31 (s,
3H), 1.31 (d, J = 7.2 Hz, 3H), 0.76(s, 9H); 13C NMR (100
MHz, CDCl3, ppm) δ 172.0, 154.7, 145.6, 137.9, 128.4, 127.8,
127.1, 124.0, 65.2, 60.8, 42.8, 36.3, 35.6, 25.4 22.3, 21.4;
HRMS (ESIꢀTOF) m/z: [M + H]+ Calcd for C18H25NO3
304.1913; Found 304.1909.
(S)-4-(tert-butyl)-3-((R)-3-(p-tolyl)butanoyl)oxazolidin-
2-one (3d, 109 mg, yield 72%): Yellow oil. Eluent: petroleum
ether/ethyl acetate (7:1). 1H NMR (400 MHz, CDCl3, ppm) δ
7.17 (d, J = 8.0 Hz, 2H), 7.08 (d, J = 8.0 Hz, 2H), 4.38 (d, J =
2.0 Hz, 1H), 4.22 (m, 2H), 3.49 (dd, J = 15.6, 7.2 Hz, 1H),
3.35 (m, 1H), 3.03 (dd, J = 16.0, 8.8 Hz, 1H), 2.30 (s, 3H),
1.31 (d, J = 6.8 Hz, 3H), 0.77(s, 9H); 13C NMR (100 MHz,
CDCl3, ppm) δ 172.0, 154.7, 142.7, 135.8, 129.1, 126.9, 65.2,
60.8, 43.0, 36.0, 35.7, 25.5, 22.3, 21.0; HRMS (ESIꢀTOF) m/z:
[M + H]+ Calcd for C18H25NO3 304.1913; Found 304.1912.
(S)-4-(tert-butyl)-3-((R)-3-(3-
(trifluoromethyl)phenyl)butanoyl)oxazolidin-2-one (3g, 142
mg, yield 80%): White solid, mp 50ꢀ51 °C. Eluent: petroleum
ether/ethyl acetate (6:1). 1H NMR (400 MHz, CDCl3, ppm) δ
7.42 (m, 4H), 4.37 (d, J = 2.0 Hz, 1H), 4.23 (m, 2H), 3.59 (dd,
J = 16.4, 8.0 Hz, 1H), 3.51 (m, 1H), 2.99 (dd, J = 16.0, 6.0 Hz,
1H), 1.35 (d, J = 7.2 Hz, 3H), 0.72(s, 9H); 13C NMR (100
MHz, CDCl3, ppm) δ 171.5, 154.6, 146.6, 130.7 (q, J = 31.5
Hz), 130.6, 128.9, 124.0 (d, J = 3.8 Hz), 123.3 (d, J = 3.7 Hz),
125.7 (q, J = 270.5 Hz), 65.2, 60.8, 42.8, 36.2, 35.5, 25.3, 22.1;
HRMS (ESIꢀTOF) m/z: [M + H]+ Calcd for C18H22F3NO3
358.1630; Found 358.1628.
(S)-4-(tert-butyl)-3-((R)-3-(4-
chlorophenyl)butanoyl)oxazolidin-2-one (3k, 111 mg, yield
69%): White solid, mp 64ꢀ65 °C. Eluent: petroleum ether/ethyl
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acetate (6:1). H NMR (400 MHz, CDCl3, ppm) δ 7.23 (m,
4H), 4.37 (dd, J = 7.6, 1.6 Hz, 1H), 4.21 (m, 2H), 3.50 (dd, J
= 16.0, 6.8 Hz, 1H), 3.39 (m, 1H), 2.97 (dd, J = 16.0, 6.4 Hz,
1H), 1.31 (d, J = 6.8 Hz, 3H), 0.76(s, 9H); 13C NMR (100
MHz, CDCl3, ppm) δ 171.7, 154.7, 144.2, 132.0, 128.5, 128.5,
65.2, 60.8, 42.9, 35.8, 35.5, 25.4, 22.2; HRMS (ESIꢀTOF) m/z:
[M + H]+ Calcd for C17H23NO3Cl 324.1366; Found
324.1366.
3-((R)-4-((S)-4-(tert-butyl)-2-oxooxazolidin-3-yl)-4-
oxobutan-2-yl)benzonitrile (3l, 124 mg, yield 79%): Yellow
oil. Eluent: petroleum ether/ethyl acetate (6:1). H NMR (400
MHz, CDCl3, ppm) δ 7.50 (m, 2H), 7.40 (d, J = 7.6 Hz, 1H),
7.32 (t, J = 7.6 Hz, 1H), 4.31 (dd, J = 7.2, 1.6 Hz, 1H), 4.18
(m, 2H), 3.41 (m, 2H), 2.95 (dd, J = 15.6, 5.6 Hz, 1H), 1.27 (d,
J = 6.8 Hz, 3H), 0.68(s, 9H); 13C NMR (100 MHz, CDCl3,
ppm) δ 171.2, 154.7, 147.2, 131.7, 131.0, 130.2, 129.3, 118.9,
112.4, 65.3, 60.2, 42.8, 35.8, 35.5, 25.44, 21.9; HRMS (ESIꢀ
TOF) m/z: [M + H]+ Calcd for C18H23N2O3 315.1709;
Found 315.1708.
4-((R)-4-((S)-4-(tert-butyl)-2-oxooxazolidin-3-yl)-4-
oxobutan-2-yl)benzonitrile (3m, 135 mg, yield 86%): White
solid, mp 90ꢀ91 °C. Eluent: petroleum ether/ethyl acetate (6:1).
1H NMR (400 MHz, CDCl3, ppm) δ 7.59 (dd, J = 6.4, 1.6 Hz,
2H), 7.40 (dd, J = 6.4, 1.6 Hz, 2H), 4.37 (dd, J = 7.2, 1.6 Hz,
1H), 4.21 (m, 2H), 3.53 (m, 2H), 3.03 (dd, J = 16, 6 Hz, 1H),
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(S)-4-(tert-butyl)-3-((R)-3-(4-
(trifluoromethyl)phenyl)butanoyl)oxazolidin-2-one
(3h,
146 mg, yield 82%): White solid, mp 86ꢀ87 °C. Eluent: petroꢀ
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