(S)-methyl 3-(3-amino-2-oxoazepan-1-yl)propanoate → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((S)-1-(3-methoxy-3-oxopropyl)-2-oxoazepan-3-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529573Notes

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][CH2:46][CH2:45][N:44]([CH2:49][CH2:50][C:51]([O:53][CH3:54])=[O:52])[C:43]1=[O:55]>>[CH2:34]([C@@H:14]([CH2:13][CH2:12][C@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([NH:41][C@H:42]1[CH2:48][CH2:47][CH2:46][CH2:45][N:44]([CH2:49][CH2:50][C:51]([O:53][CH3:54])=[O:52])[C:43]1=[O:55])=[O:10])[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:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Reactant 2

HCID 68309766(S)-methyl 3-(3-amino-2-oxoazepan-1-yl)propanoate

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

Product 1

HCID 68310950(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((S)-1-(3-methoxy-3-oxopropyl)-2-oxoazepan-3-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-((S)-1-(3-methoxy-3-oxopropyl)-2-oxoazepan-3-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 Intermediate 27 (4.4 mg, 0.018 mmol) to give a white solid (2.1 mg, 29% yield). Anal. Calcd. for C41H54N4O8S m/z 762.5. found: 763.5 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 7.26-7.06 (m, 10H), 5.50 (d, J=3.3 Hz, 1H), 5.15 (d, J=6.6 Hz, 1H), 4.98 (dd, J=8.8, 4.4 Hz, 1H), 4.44 (d, J=11.0 Hz, 1H), 3.67-3.62 (m, 6H), 3.62-3.48 (m, 2H), 3.36 (dd, J=15.4, 4.4 Hz, 1H), 3.12 (d, J=9.3 Hz, 1H), 2.89-2.72 (m, 3H), 2.72-2.59 (m, 4H), 2.59-2.50 (m, 2H), 2.36 (d, J=12.1 Hz, 1H), 2.06 (d, J=7.1 Hz, 1H), 1.97 (d, J=11.5 Hz, 1H), 1.87 (d, J=12.1 Hz, 1H), 1.84-1.54 (m, 10H), 1.54-1.40 (m, 2H), 1.39-1.27 (m, 2H).

Sources & evidence

ORD record: ord-07cf0c71908e4f03bfa766b5bb238a1e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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