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

HRID 529613Notes

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][CH2:54][CH2:53][CH2:52][N:51]([C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([O:62][CH3:63])[CH:57]=2)[C:50]1=[O:64]>>[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:48][C@H:49]1[CH2:55][CH2:54][CH2:53][CH2:52][N:51]([C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([O:62][CH3:63])[CH:57]=2)[C:50]1=[O:64])=[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 68292672(S)-3-Amino-1-(3-methoxyphenyl)azepan-2-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 86706253(4S,7S,10aS)-Methyl 4-((2R,5R)-2,5-dibenzyl-6-((S)-1-(3-methoxyphenyl)-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-(3-methoxyphenyl)-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 (24 mg, 0.042 mmol) and Intermediate 65 (19 mg, 0.055 mmol) to give a white solid (21 mg, 62% yield). Anal. Calcd. for C44H54N4O7S m/z 782.7. found: 783.7 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.36-7.02 (m, 11H), 6.83 (dd, J=8.2, 2.1 Hz, 1H), 6.69 (dt, J=4.2, 1.6 Hz, 2H), 6.42 (s, 2H), 5.32 (t, J=4.6 Hz, 1H), 5.17-5.07 (m, 1H), 5.04-4.91 (m, 1H), 4.76 (dd, J=9.7, 6.9 Hz, 1H), 3.98 and 3.78 (2s, 3H), 3.93 (dd, J=15.4, 11.6 Hz, 1H), 3.68 (s, 3H), 3.63-3.54 (m, 1H), 3.16-3.06 (m, 1H), 2.90-2.67 (m, 5H), 2.53-2.32 (m, 3H), 2.07-1.79 (m, 5H), 1.79-1.43 (m, 11H), 1.40-1.23 (m, 1H).

Sources & evidence

ORD record: ord-03355fc7f0e34d829a9ad64f77245088
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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