Potassium Bromide → HCID 18469096, compound

HRID 1182525Notes

Reaction equation

[CH3:1][C:2]1[N:7]([CH2:8][C:9]([NH:11][CH:12]2[CH2:16][C:15](=[O:17])[O:14][CH:13]2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:10])[C:6](=[O:26])[C:5]([NH:27][C:28](=[O:37])[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:4][CH:3]=1.[K+].[Br-]>>[O:26]=[C:6]1[C:5]([NH:27][C:28](=[O:37])[CH2:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:4][CH:3]=[C:2]([C:1]2[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=2)[N:7]1[CH2:8][C:9]([NH:11][CH:12]1[CH2:16][C:15](=[O:17])[O:14][CH:13]1[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:10]

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 18468996HCID 18468996, compound

Product 1

HCID 18469096HCID 18469096, compoundYield 53%

Procedure

N(3(S)) 2[1,2-Dihydro-6-methyl-2-oxo-3-(3-phenylpropionyl)amino-1-pyridyl]-N-(2-benzyloxy-5-oxotetrahydrofuran-3-yl)acetamide (53e), was obtained (67%) as a mixture of anomers: IR (KBr) 3282, 1774, 1667, 1651, 1596, 1561, 1556, 1498, 1265, 1254, 1236, 1199, 1143; 1H NMR (d6-DMSO) δ 9.17 and 9.15 (1H, 2×s), 8.89 (0.5H, d, J=6.5), 8.73 (0.5H, d, J=7.4), 7.25 (10H, m), 6.13 (1H, t), 5.64 (0.5H, d, J=5.0), 5.45 (0.5H, s), 4.89-4.61 (4.5H, m), 4.26 (0.5H, m), 3.17-2.36 (6H, m), 2.23 and 2.15 (3H, 2s). N(3(S)) 2-[1,2-Dihydro-2-oxo-6-phenyl-3(3-phenylpropionyl)amino-1-pyridyl]-N-(2-benzyloxy-5-oxotetrahydrofuran-3-yl)acetamide (53%), was obtained (73%) as a mixture of anomers: IR (KBr) 3296, 1792, 1691, 1643, 1595, 1561, 1514, 1489, 1453, 1420, 1373, 1230, 1118; 1H NMR (d6-DMSO) δ 9.40, 9.36 (1H, 2s), 8.70 (0.5H, d, J=7.6), 8.52 (0.5H, d, J=7.5), 8.29 (1H, dd), 7.25 (15H, m), 6.20 (1H, d, J=7.6), 5.61 (0.5H, d, J=5.0), 5.28 (0.5H, s), 4.78-4.20 (5H, m), 3.12-2.24 (6H, m). N(3(S)) 2-[1,2-Dihydro-2-oxo-3-(3-phenylpropionyl) amino-1-pyridyl]-N-(2-benzyloxy-5-oxotetrahydrofuran-3-yl)acetamide (53g), was obtained (70%) as a mixture of anomers: IR (KBr) 3336, 3290, 1791, 1691, 1646, 1595, 1582, 1556, 1518, 1454, 1376, 1351, 1150, 1122; 1H NMR (d6-DMSO) δ 9.26 (1H, 2s), 8.86 (0.5H, d, J=6.4), 8.67 (0.5H, d, J=7.5), 8.23 (1H, m), 7.40-7.13 (11H, m), 6.24 (1H, 2t, J=7.2), 5.61 (0.5H, d, J=5.0), 5.44 (0.5H, s), 4.83-4.59 (2.5H, m), 4.25 (0.5H, m), 3.15-2.34 (2H, m), 2.91-2.70 (4H, m). Anal. Calc. for C27H27N3O6 H2O: C, 63.90; H, 5.76; N, 8.28. Found: C 63.70; H, 5.68; N, 8.22. MS FAB M+=490 (M +1). 2(R,S), N(3(S)) 2-[6-Benzyl-1,2-dihydro-2-oxo-3-(3-phenylpropionyl)amino-1-pyridyl]-N(2-benzyloxy-5-oxotetrahydrofuran-3-yl)propionamide (53h), was obtained (89%) as a mixture of diastereomers. Data is given for a single diastereomer: IR (film) 3356, 1788, 1677, 1645, 1602, 1517, 1455, 1377, 1203, 1167, 1120;

Workup

additionas a mixture of anomers

Sources & evidence

ORD record: ord-0cb9117b6a8d46bab1921ff75fbe93d0
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288624B2

Reaction notes

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