(4S,7S,10aS)-4-Amino-7-(methoxymethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one hydrochloride → (2R,5R)-2,5-Dibenzyl-N1-((4S,7S,10aS)-7-(methoxymethyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((S)-2-oxo-1-phenylazepan-3-yl)hexanediamide

HRID 529616Notes

Reaction equation

HRID 529616 reaction equation
[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:15](=[O:31])[NH:16][C@@H:17]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]1=[O:30])[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:40][C@H:41]1[CH2:47][CH2:46][S:45][C@H:44]2[CH2:48][CH2:49][CH2:50][C@@H:51]([CH2:52][O:53][CH3:54])[N:43]2[C:42]1=[O:55]>>[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:15]([NH:16][C@H:17]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]1=[O:30])=[O:31])[C:9]([NH:40][C@H:41]1[CH2:47][CH2:46][S:45][C@H:44]2[CH2:48][CH2:49][CH2:50][C@@H:51]([CH2:52][O:53][CH3:54])[N:43]2[C:42]1=[O:55])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 68292741(4S,7S,10aS)-4-Amino-7-(methoxymethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one hydrochlorideHCID 86706193(2R,5R)-2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoic acid

Product 1

HCID 66546463(2R,5R)-2,5-Dibenzyl-N1-((4S,7S,10aS)-7-(methoxymethyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((S)-2-oxo-1-phenylazepan-3-yl)hexanediamide

Procedure

(2R,5R)-2,5-Dibenzyl-N1-((4S,7S,10aS)-7-(methoxymethyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-N6-((S)-2-oxo-1-phenylazepan-3-yl)hexanediamide was synthesized as described in General Procedure H using Intermediate 24 (10 mg, 0.020 mmol) and Intermediate 66 (6.6 mg, 0.023 mmol) to give a white solid (7.6 mg, 53% yield). Anal. Calcd. for C43H54N4O5S m/z 738.7. found: 739.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.38 (2H, t, J=7.8 Hz), 7.30-7.18 (3H, m), 7.18-7.09 (8H, m), 6.91 (1H, d, J=6.4 Hz), 6.83 (1H, d, J=6.4 Hz), 5.29-5.19 (1H, m), 4.96-4.87 (1H, m), 4.76 (1H, dd, J=9.9, 6.6 Hz), 4.71-4.64 (1H, m), 3.95 (1H, dd, J=15.1, 11.9 Hz), 3.70 (1H, t, J=9.4 Hz), 3.60 (1H, dd, J=15.1, 4.6 Hz), 3.40-3.31 (4H, m), 3.22-3.12 (1H, m), 2.90-2.78 (2H, m), 2.75-2.60 (3H, m), 2.40-2.30 (2H, m), 2.06-1.92 (4H, m), 1.91-1.79 (3H, m), 1.79-1.43 (9H, m), 1.36-1.24 (2H, m).

Sources & evidence

ORD record
ord-a4c36012af8f46759d5007aaa1879c61
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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