3-Amino-4,4-dimethyl-1-phenylazepan-2-one → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((S)-4,4-dimethyl-2-oxo-1-phenylazepan-3-ylamino)-6-oxohexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529579Notes

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][CH:42]1[C:48]([CH3:50])([CH3:49])[CH2:47][CH2:46][CH2:45][N:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:43]1=[O:57]>>[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[C:48]([CH3:50])([CH3:49])[CH2:47][CH2:46][CH2:45][N:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:43]1=[O:57])=[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 682916973-Amino-4,4-dimethyl-1-phenylazepan-2-one

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 68309859(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((S)-4,4-dimethyl-2-oxo-1-phenylazepan-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)-4,4-dimethyl-2-oxo-1-phenylazepan-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 (10 mg, 0.018 mmol) and Intermediate 34 (4.1 mg, 0.018 mmol) to give a white solid (4.0 mg, 27% yield). Anal. Calcd. for C45H56N4O6S m/z 780.4. found: 781.5 (M+H)+; 1H NMR (500 MHz, CD3OD) δ ppm 7.32 (t, J=7.70 Hz, 2H), 7.28-7.10 (m, 11H), 7.00 (d, J=7.70 Hz, 2H), 5.52 (dd, J=6.05, 2.75 Hz, 1H), 5.07-4.97 (m, 2H), 4.94-4.88 (m, 1H), 4.12-4.00 (m, 1H), 3.60 (s, 3H), 3.58-3.51 (m, 1H), 2.98-2.82 (m, 2H), 2.82-2.63 (m, 5H), 2.59-2.50 (m, 1H), 2.38-2.27 (m, 1H), 2.13-2.02 (m, 1H), 1.97 (br. s., 2H), 1.86-1.75 (m, 3H), 1.75-1.55 (m, 7H), 1.48 (s, 1H), 1.32-1.24 (m, 1H), 0.80 (s, 3H), 0.45 (s, 3H).

Sources & evidence

ORD record: ord-3f630ca8adb34c4d8785fb3f95b3174d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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