(4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate → Methyl (4S,7S,10aS)-4-(((2S,5R)-5-benzyl-2-ethyl-6-(((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepin-4-yl)amino)-6-oxohexanoyl)amino)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529636Notes

Reaction equation

HRID 529636 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:18][CH3:19])[C:15]([OH:17])=O)[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C@H:21]1[CH2:27][CH2:26][S:25][C@H:24]2[CH2:28][CH2:29][CH2:30][C@@H:31]([C:32]([O:34][CH3:35])=[O:33])[N:23]2[C:22]1=[O:36]>>[CH2:1]([C@H:8]([C:9]([NH:20][C@H:21]1[CH2:27][CH2:26][S:25][C@H:24]2[CH2:28][CH2:29][CH2:30][C@@H:31]([C:32]([O:34][CH3:35])=[O:33])[N:23]2[C:22]1=[O:36])=[O:11])[CH2:12][CH2:13][C@H:14]([CH2:18][CH3:19])[C:15]([NH:20][C@H:21]1[CH2:27][CH2:26][S:25][C@H:24]2[CH2:28][CH2:29][CH2:30][C@@H:31]([C:32]([O:34][CH3:35])=[O:33])[N:23]2[C:22]1=[O:36])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10563170(4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylateHCID 68292029(2R,5S)-2-benzyl-5-ethylhexanedioic acid

Product 1

HCID 86706266Methyl (4S,7S,10aS)-4-(((2S,5R)-5-benzyl-2-ethyl-6-(((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepin-4-yl)amino)-6-oxohexanoyl)amino)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Procedure

Methyl (4S,7S,10aS)-4-(((2S,5R)-5-benzyl-2-ethyl-6-(((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepin-4-yl)amino)-6-oxohexanoyl)amino)-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate was synthesized as described in General Procedure F using Intermediate 82 (33 mg, 0.13 mmol) and (4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (121 mg, 0.312 mmol) to give a white solid (25 mg, 27% yield). Anal. Calcd. for C37H52N4O8S2 m/z 744.3. found: 745.3 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.47 (m, 1H), 7.23-7.13 (m, 5H), 5.40-5.30 (m, 2H), 5.19-5.12 (m, 3H), 4.99 (m, 1H), 3.73 (s, 3H), 3.69 (s, 3H), 3.28-3.12 (m, 2H), 2.92-2.71 (m, 14H), 2.41 (m, 3H), 2.24 (m, 1H), 2.05-1.98 (m, 6H), 1.80-1.44 (m, 14H), 0.86 (t, J=7.4 Hz, 3H).

Sources & evidence

ORD record
ord-7aa6f0cfdf074431b3e5e079cd81275c
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

Loading…