5
418 J . Org. Chem., Vol. 66, No. 16, 2001
-(F u r a n -2-yl-h yd r oxy-m eth yl)-a cr ylic Acid , 1-Meth yl
Yu et al.
2
5.60 (d, J ) 5.2 Hz, 1H), 5.05-4.60 (br s, 1H, OH), 3.69 (s,
1
13
Ester (26). H NMR (CDCl
3
): δ 7.37-7.35 (m, 1H), 6.39-6.37
3
3H). C NMR (CDCl ): δ 166.7, 159.8, 148.4, 141.9, 137.0,
(
1
m, 1H), 6.34-6.31 (m, 1H), 6.25-6.23 (m, 1H), 5.96 (t, J )
127.0, 122.8, 121.5, 72.3, 52.0. IR (neat): ν 3418, 3011, 2953,
-
1
+
.1 Hz, 1H), 5.59 (d, J ) 5.2 Hz, 1H), 3.75 (s, 3H), 3.43 (d, J
1722, 1593 cm . ESIMS m/z (relative intensity): 194.05 (MH ,
1
3
)
1
1
5.8 Hz, 1H). C NMR (CDCl
3
): δ 166.6, 154.3, 142.5, 139.7,
100), 175.99 (79). HRMS (ESI) m/z: calcd for C10
H
12NO
3
+
26.9, 110.6, 107.4, 67.2, 52.2. IR (neat): ν 3436, 1713, 1631,
(MH ), 194.0817; found, 194.0822.
-1
436, 1282, 1149 cm . ESIMS m/z (relative intensity): 164.96
(M - OH),
2-(Hyd r oxy-p yr id in -3-yl-m eth yl)-a cr ylic Acid , 1-Meth -
yl Ester (38).
(
1
M - OH, 100). HRMS (ESI) m/z: calcd for C
9
H
9
O
3
1
H NMR (CDCl ): δ 8.37 (br s, 1H), 8.26 (d, J
3
65.0552; found, 165.0560.
-[H yd r oxy-(5-h yd r oxym e t h yl-fu r a n -2-yl)-m e t h yl]-
) 3.6 Hz, 1H), 7.65 (d, J ) 7.8 Hz, 1H), 7.16 (dd, J ) 4.8, 8.0
2
Hz, 1H), 6.30 (s, 1H), 5.97 (s, 1H), 5.21 (s, 1H), 5.16 (br s, 1H),
1
13
a cr ylic Acid , 1-Meth yl Ester (28). H NMR (CDCl
3
): δ 6.39
s, 1H), 6.19 (d, J ) 3.4 Hz, 1H), 6.14 (d, J ) 3.0 Hz, 1H), 6.02
s, 1H), 5.57 (br s, 1H), 4.50 (s, 2H), 3.99 (d, J ) 4.8 Hz, 1H,
3.60 (s, 3H). C NMR (CDCl ): δ 166.4, 148.4, 148.4, 142.1,
138.1, 135.1, 126.1, 123.7, 70.4, 52.1. IR (neat): ν 3180, 1718,
1626, 1436 cm-1. ESIMS m/z (relative intensity): 195.13 (M
3
(
(
1
3
+
+
OH), 3.74 (s, 3H), 3.21 (br s, 1H, OH). C NMR (CDCl
3
): δ
+ 2H , 10), 194.02 (MH , 100). HRMS (ESI) m/z: calcd for
1
66.7, 154.3, 154.1, 139.5, 127.0, 108.8, 108.2, 66.7, 57.3, 52.3.
C H NO (MH
+
), 194.0817; found, 194.0834.
1
0
12
3
-1
IR (neat): ν 3385, 1708, 1631, 1436 cm . ESIMS m/z (relative
2
-{H yd r oxy-[6-(1-h yd r oxy-2-m et h oxyca r b on yl-a llyl)-
p yr id in -2-yl]-m eth yl}-a cr ylic Acid , 1-Meth yl Ester (40).
): δ 7.64 (t, J ) 7.7 Hz, 1H), 7.26 (d, J ) 7.6
Hz, 2H), 6.25 (s, 2H), 5.82 (s, 2H), 5.53 (s, 2H), 4.55 (br s, 2H,
+
intensity): 235.07 (M + Na , 63), 195.04 (M - OH, 100).
+
HRMS (ESI) m/z: calcd for C10
H
16NO
5
(M + NH
4
), 230.1028;
1
H NMR (CDCl
3
found, 230.1036.
2
-[Hyd r oxy-(5-n itr o-fu r a n -2-yl)-m eth yl]-a cr ylic Acid ,
13
OH), 3.64 (s, 6H). C NMR (CDCl ): δ 166.8, 158.7, 158.7,
3
1
1
-Meth yl Ester (30). H NMR (CDCl
H), 6.53 (d, J ) 3.6 Hz, 1H), 6.48 (s, 1H), 6.09 (s, 1H), 5.60
3
): δ 7.27 (d, J ) 4.4 Hz,
1
1
3
41.6, 137.9, 127.0, 120.3, 120.3, 72.6, 52.1. IR (neat): ν 3423,
1
-1
716, 1633, 1594, 1577 cm . ESIMS m/z (relative intensity):
(
(
s, 1H), 4.05-3.80 (br s, 1H, OH), 3.76 (s, 3H). 13C NMR
+
08.14 (MH , 100), 272.09 (16). HRMS (ESI) m/z: calcd for
CDCl
3
): δ 166.1, 158.1, 151.8, 137.8, 128.9, 112.8, 110.6, 67.4,
+
C
15
H
18NO
6
(MH ), 308.1134; found, 308.1132.
-1
5
2.6. IR (neat): ν 3470, 1716, 1531, 1497, 1356 cm . ESIMS
1
Beta in e 44a . Mp 172-174 °C (sublimated at 163 °C). H
NMR (D O): δ 3.40 (s, 2H), 3.29 (t, J ) 7.1 Hz, 6H), 3.08 (t, J
7.2 Hz, 6H). C NMR (D
2.4, 27.8 (p, J ) 17.4 Hz, C-D). IR (neat): ν 1597, 1365
+
m/z (relative intensity): 250.03 (M + Na , 100). HRMS (ESI)
2
+
m/z: calcd for C
45.0774.
-(Hyd r oxy-th ia zol-2-yl-m eth yl)-a cr ylic Acid , 1-Meth yl
9
H
13
N
2
O
6
(M + NH
4
), 245.0774; found,
13
)
2
O + DMSO-d ): δ 173.9, 59.6, 50.2,
6
2
13
4
2
-1
+
cm . ESIMS m/z (relative intensity): 187.14 (MH , 93), 373.30
1
Ester (32). H NMR (CDCl
3
): δ 7.68 (d, J ) 3.0 Hz, 1H), 7.30
+
(
(
2M + H , 38). HRMS (FAB) m/z: calcd for C
9
H
15
D
2
N
2
O
2
(
(
d, J ) 3.4 Hz, 1H), 6.42 (s, 1H), 6.03 (d, J ) 1.0 Hz, 1H), 5.79
+
MH ), 187.1414; found, 187.1408.
1
3
br s, 1H), 4.98 (br s, 1H), 3.74 (s, 3H). C NMR (CDCl
3
): δ
1
Beta in e 44b. Mp 151 °C (sublimation). H NMR (D
2
O): δ
1
72.9, 166.5, 142.5, 139.9, 128.0, 119.9, 71.3, 52.3. IR (neat):
3
.45-3.36 (m, 2H), 3.26 (t, J ) 3.8 Hz, 6H), 3.09 (d, J ) 5.2
-
1
ν 3210, 2944, 1718, 1631, 1436 cm . ESIMS m/z (relative
intensity): 222.02 (M + Na , 20), 200.00 (MH , 100). HRMS
1
3
Hz, 6H), 2.55 (t, J ) 7.6 Hz, 2H). C NMR (D
2
O + DMSO-d
6
-
):
+
+
1
δ 173.1, 60.1, 50.3, 42.7, 28.6. IR (neat): ν 1596, 1360 cm
.
+
(
2
ESI) m/z: calcd for C
00.0356.
-[H y d r o x y -(1-m e t h y l-1H -im id a zo l-2-y l)-m e t h y l]-
8 3
H10NO S (MH ), 200.0381; found,
+
ESIMS m/z (relative intensity): 185.19 (MH , 100), 369.31 (2M
+
+
H , 10).
2
1
a cr ylic Acid , 1-Meth yl Ester (34). H NMR (CDCl
3
): δ 6.90
(s, 1H), 6.81 (s, 1H), 6.41 (s, 1H), 5.95 (s, 1H), 5.64 (s, 1H),
Ack n ow led gm en t. We gratefully acknowledge the
3
1
1
1
1
.75 (d, J ) 2.2 Hz, 3H), 3.72 (d, J ) 2.2 Hz, 3H), 2.89 (d, J )
financial support of grant GM 62752 from the National
Institutes of Health.
1
3
.8 Hz, 1H). C NMR (CDCl
3
): δ 166.8, 140.0, 127.2, 126.1,
21.8, 65.9, 52.2, 46.4, 33.3. IR (neat): ν 3448, 3039, 2851, 2724,
-
1
+
712 cm . ESIMS m/z (relative intensity): 198.16 (M + 2H ,
Su p p or tin g In for m a tion Ava ila ble: Kinetic analysis of
+
0), 197.05 (MH , 100). HRMS (ESI) m/z: calcd for C
9
H
13
N
2
O
3
1
the reaction between DABCO and methyl acrylate using H
+
(MH ), 197.0926; found, 197.0953.
NMR and spectroscopic data for new compounds 4, 14, 20, 24,
2
-(Hyd r oxy-p yr id in -2-yl-m eth yl)-a cr ylic Acid , 1-Meth -
2
6, 28, 30, 32, 34, 36, 38, 40, 44a , and 44b. This material is
1
yl Ester (36). H NMR (CDCl
.66-7.61 (m, 1H), 7.39 (d, J ) 7.4 Hz, 1H), 7.17 (t, J ) 6.1
Hz, 1H), 6.32 (d, J ) 5.4 Hz, 1H), 5.93 (d, J ) 5.9 Hz, 1H),
3
): δ 8.49 (d, J ) 4.8 Hz, 1H),
available free of charge via the Internet at http://pubs.acs.org.
7
J O015628M