(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 → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((4R,7S,10aR)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529581Notes

Reaction equation

HRID 529581 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:15]([NH:17][C@H:18]1[CH2:24][CH2:23][S:22][C@H:21]2[CH2:25][CH2:26][CH2:27][C@@H:28]([C:29]([O:31][CH3:32])=[O:30])[N:20]2[C:19]1=[O:33])=[O:16])[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:41][C@@H:42]1[CH2:48][CH2:47][S:46][C@@H:45]2[CH2:49][CH2:50][CH2:51][C@@H:52]([C:53]([O:55][CH3:56])=[O:54])[N:44]2[C:43]1=[O:57]>>[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:15]([NH:17][C@@H:18]1[CH2:24][CH2:23][S:22][C@@H:21]2[CH2:25][CH2:26][CH2:27][C@@H:28]([C:29]([O:31][CH3:32])=[O:30])[N:20]2[C:19]1=[O:33])=[O:16])[C:9]([NH:41][C@H:42]1[CH2:48][CH2:47][S:46][C@H:45]2[CH2:49][CH2:50][CH2:51][C@@H:52]([C:53]([O:55][CH3:56])=[O:54])[N:44]2[C:43]1=[O:57])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

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 acidHCID 86706243HCID 86706243, compound

Product 1

HCID 68311036(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((4R,7S,10aR)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Procedure

(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((4R,7S,10aR)-7-(methoxycarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate was synthesized as described in General Procedure H using Intermediate 23 (5.0 mg, 0.0088 mmol) and (4R,7S,10aR)-methyl 4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (2.2 mg, 0.0097 mmol) to give a white solid (3.2 mg, 40% yield). Anal. Calcd. for C42H54N4O8S2 m/z 806.4. found: 807.4 (M+H)+.

Sources & evidence

ORD record
ord-ca879de066a84f55bd0d67a0136bd929
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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