(S,Z)-3-Amino-1-phenyl-3,4-dihydro-1H-azepin-2(7H)-one trifluoroacetate → (4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S,Z)-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

HRID 529601Notes

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.FC(F)(F)C(O)=O.[NH2:48][C@H:49]1[CH2:55][CH:54]=[CH:53][CH2:52][N:51]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]1=[O:62]>>[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](=[O:10])[NH:48][C@H:49]1[CH2:55][CH:54]=[CH:53][CH2:52][N:51]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]1=[O:62])[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 68292369(S,Z)-3-Amino-1-phenyl-3,4-dihydro-1H-azepin-2(7H)-one trifluoroacetate

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 68311192(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S,Z)-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate

Procedure

(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-oxo-6-((S,Z)-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylamino)hexanamido)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate was synthesized as described in General Procedure H using Intermediate 23 (30 mg, 0.053 mmol) and Intermediate 52 (20 mg, 0.064 mmol) to give a white solid (26 mg, 65% yield). Anal. Calcd. for C43H50N4O6S m/z 750.4. found: 751.4 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.86 (dd, J=36.0, 7.3 Hz, 2H), 7.34 (t, J=7.8 Hz, 2H), 7.26-7.06 (m, 11H), 6.02-5.84 (m, 1H), 5.79-5.66 (m, 1H), 5.65-5.56 (m, 1H), 5.28-5.12 (m, 1H), 5.01 (d, J=4.4 Hz, 2H), 4.82 (d, J=17.7 Hz, 1H), 3.78 (dd, J=17.8, 7.9 Hz, 1H), 3.17-2.93 (m, 2H), 2.93-2.36 (m, 11H), 2.25-2.04 (m, 2H), 2.04-1.87 (m, 2H), 1.87-1.73 (m, 1H), 1.72-1.38 (m, 7H), 1.32 (d, J=6.2 Hz, 2H).

Sources & evidence

ORD record: ord-34ed3fe707194b6e859f79323c946921
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

Loading…