(4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate → (2R,5R)-2,5-Dibenzyl-6-((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-6-oxohexanoic acid

HRID 529453Notes

Reaction equation

HRID 529453 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15](O)=[O:16])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][C@H:26]1[CH2:32][CH2:31][S:30][C@H:29]2[CH2:33][CH2:34][CH2:35][C@@H:36]([C:37]([O:39][CH3:40])=[O:38])[N:28]2[C:27]1=[O:41]>>[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:15]([NH:25][C@H:26]1[CH2:32][CH2:31][S:30][C@H:29]2[CH2:33][CH2:34][CH2:35][C@@H:36]([C:37]([O:39][CH3:40])=[O:38])[N:28]2[C:27]1=[O:41])=[O:16])[C:9]([OH:11])=[O:10])[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 68292409(2R,5R)-2,5-dibenzylhexanedioic acid

Product 1

HCID 68311179(2R,5R)-2,5-Dibenzyl-6-((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-6-oxohexanoic acid

Procedure

(2R,5R)-2,5-Dibenzyl-6-((4S,7S,10aS)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-6-oxohexanoic acid was synthesized as described in General Procedure G using (2R,5R)-2,5-dibenzylhexanedioic acid (200 mg, 0.613 mmol) and (4S,7S,10aS)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (249 mg, 0.643 mmol) to give a white solid (278 mg, 80% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.31-7.09 (10H, m), 6.88 (1H, d, J=6.6 Hz), 5.30 (1H, t, J=4.7 Hz), 5.17-5.11 (1H, m), 5.07-4.98 (1H, m), 3.68 (3H, s), 3.22-3.11 (1H, m), 3.02-2.92 (1H, m), 2.90-2.81 (1H, m), 2.80-2.63 (4H, m), 2.46-2.37 (2H, m), 2.06-1.96 (2H, m), 1.86-1.75 (2H, m), 1.72-1.47 (7H, m).

Sources & evidence

ORD record
ord-14c0fc9c76614c9da728ab16f2d41831
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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