(2R,5R)-2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoic acid → (2R,5R)-2,5-Dibenzyl-N1-((S)-2-oxo-1-phenylazepan-3-yl)-N6-((4S,10aS)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

HRID 529602Notes

Reaction equation

HRID 529602 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.[NH2:39][C@H:40]1[CH2:46][CH2:45][S:44][C@H:43]2[CH2:47][CH2:48][CH2:49][CH2:50][N:42]2[C:41]1=[O:51]>>[CH2:32]([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:39][C@H:40]1[CH2:46][CH2:45][S:44][C@H:43]2[CH2:47][CH2:48][CH2:49][CH2:50][N:42]2[C:41]1=[O:51])=[O:10])[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:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 86706193(2R,5R)-2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoic acidHCID 86706213(4S,10aS)-4-aminohexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

Product 1

HCID 68311231(2R,5R)-2,5-Dibenzyl-N1-((S)-2-oxo-1-phenylazepan-3-yl)-N6-((4S,10aS)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide

Procedure

(2R,5R)-2,5-Dibenzyl-N1-((S)-2-oxo-1-phenylazepan-3-yl)-N6-((4S,10aS)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)hexanediamide was synthesized as described in General Procedure H using Intermediate 24 (20 mg, 0.039 mmol) and Intermediate 40 (10 mg, 0.051 mmol) to give a white solid (16 mg, 58% yield). Anal. Calcd. for C41H50N4O4S m/z 694.4. found: 695.3 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.76 (dd, J=18.7, 7.1 Hz, 2H), 7.35 (t, J=7.8 Hz, 2H), 7.29-7.03 (m, 11H), 5.60 (s, 1H), 5.04-4.85 (m, 1H), 4.76-4.59 (m, 1H), 4.08 (d, J=13.2 Hz, 1H), 3.95 (dd, J=15.3, 11.5 Hz, 1H), 3.52 (d, J=15.9 Hz, 1H), 3.07 (t, J=11.3 Hz, 1H), 2.87-2.35 (m, 11H), 2.08-1.01 (m, 17H).

Sources & evidence

ORD record
ord-99fb2039956a42f2a783d2f0253720e9
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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