(S)-3-amino-1-o-tolylazepan-2-one → (2R,5R)-2,5-Dibenzyl-6-oxo-6-((S)-2-oxo-1-o-tolylazepan-3-ylamino)hexanoic acid

HRID 529544Notes

Reaction equation

HRID 529544 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][CH2:22][CH2:21][N:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2OC)[C:19]1=[O:33])=[O:16])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@H:42]1CCCCN(C2C=CC=CC=2C)C1=O>>[CH2:1]([C@@H:8]([CH2:12][CH2:13][C@H:14]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:15](=[O:16])[NH:17][C@H:18]1[CH2:24][CH2:23][CH2:22][CH2:21][N:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:42])[C:19]1=[O:33])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 68292218(S)-3-amino-1-o-tolylazepan-2-oneHCID 68310532(2R,5R)-2,5-dibenzyl-6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylamino)-6-oxohexanoic acid

Product 1

HCID 68292933(2R,5R)-2,5-Dibenzyl-6-oxo-6-((S)-2-oxo-1-o-tolylazepan-3-ylamino)hexanoic acid

Procedure

(2R,5R)-2,5-Dibenzyl-6-oxo-6-((S)-2-oxo-1-o-tolylazepan-3-ylamino)hexanoic acid (65 mg, 0.12 mmol) was synthesized as described for the preparation of Intermediate 70 using (S)-3-amino-1-o-tolylazepan-2-one. Anal. Calcd. for C33H38N2O4 m/z 526.4. found: 527.4 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.37-6.84 (m, 16H), 4.84-4.72 (m, 1H), 4.01-3.78 (m, 1H), 3.51 and 3.28 (dd, J=15.0, 4.8 Hz, 1H), 3.04-2.81 (m, 2H), 2.79-2.61 (m, 3H), 2.50-2.37 (m, 1H), 2.18 (s, 1H), 2.13 (s, 2H), 2.03-1.44 (m, 10H).

Sources & evidence

ORD record
ord-254b56519d0a4053b74fc825fa9dc50b
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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