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

HRID 529597Notes

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.Cl.[NH2:42][C@H:43]1[CH2:49][CH2:48][CH2:47][CH2:46][N:45]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[Cl:57])[C:44]1=[O:58]>>[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:42][C@H:43]1[CH2:49][CH2:48][CH2:47][CH2:46][N:45]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[Cl:57])[C:44]1=[O:58])=[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 68292357(S)-3-Amino-1-(2-chlorobenzyl)azepan-2-one hydrochloride

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 66546276(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((S)-1-(2-chlorobenzyl)-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-(2-chlorobenzyl)-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 (7.0 mg, 0.012 mmol) and Intermediate 48 (3.6 mg, 0.012 mmol) to give a white solid (7.0 mg, 69% yield). Anal. Calcd. for C44H53ClN4O6S m/z 800.4. found: 801.4 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 7.39-7.32 (m, 1H), 7.25-7.17 (m, 7H), 7.18-7.11 (m, 6H), 6.92 (t, J=7.70 Hz, 2H), 5.32 (t, J=4.67 Hz, 1H), 5.17-5.10 (m, 1H), 4.97 (t, J=6.87 Hz, 1H), 4.81 (d, J=15.40 Hz, 1H), 4.68-4.63 (m, 1H), 4.63-4.57 (m, 1H), 3.68 (s, 3H), 3.50 (dd, J=15.40, 11.55 Hz, 1H), 3.29-3.11 (m, 2H), 2.92-2.75 (m, 3H), 2.75-2.66 (m, 2H), 2.46-2.30 (m, 3H), 2.03-1.99 (m, 2H), 1.89-1.79 (m, 2H), 1.77-1.45 (m, 13H).

Sources & evidence

ORD record: ord-13648a771f2146f9986c95da5af1d2d6
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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