(S)-tert-Butyl 1-isobutyl-2-oxoazepan-3-ylcarbamate → (4S,7S)-Methyl 4-((2S,5S)-2,5-dibenzyl-6-((S)-1-isobutyl-2-oxoazepan-3-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529635Notes

Reaction equation

HRID 529635 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.[CH2:41]([N:45]1[CH2:51][CH2:50][CH2:49][CH2:48][C@H:47]([NH:52]C(=O)OC(C)(C)C)[C:46]1=[O:60])[CH:42]([CH3:44])[CH3:43]>>[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:52][C@H:47]1[CH2:48][CH2:49][CH2:50][CH2:51][N:45]([CH2:41][CH:42]([CH3:43])[CH3:44])[C:46]1=[O:60])=[O:10])[C:15]([NH:17][C@H:18]1[CH2:24][CH2:23][S:22][CH: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

3

Reactant 2

HCID 68310529(S)-tert-Butyl 1-isobutyl-2-oxoazepan-3-ylcarbamateHCID 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 86706265(4S,7S)-Methyl 4-((2S,5S)-2,5-dibenzyl-6-((S)-1-isobutyl-2-oxoazepan-3-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Procedure

(4S,7S)-Methyl 4-((2S,5S)-2,5-dibenzyl-6-((S)-1-isobutyl-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 (40 mg, 0.070 mmol) and Intermediate 80 (26 mg, 0.088 mmol) to give a white solid (40 mg, 77% yield). Anal. Calcd. for C41H56N4O6S m/z 732.4. found: 733.4 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.90 (d, J=7.3 Hz, 2H), 7.67 (d, J=6.8 Hz, 1H), 7.18 (m, 10H), 6.96 (m, 1H), 6.48 (m, 1H), 5.62 (m, 1H), 5.15 (m, 1H), 5.02 (m, 1H), 4.45 (m, 1H), 3.75 (m, 1H), 3.57 (s, 3H), 3.49 (m, 2H), 3.20-3.00 (m, 2H), 2.79 (m, 3H), 2.63 (m, 4H), 2.80-2.57 (m, 4H), 1.82-1.59 (m, 13H), 1.26 (m, 1H), 0.81 (m, 6H).

Sources & evidence

ORD record
ord-286213c30155421c8244f1ce17c966de
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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