Benzyl 4-azido-3-hydroxyazepane-1-carboxylate → 4-(4-Morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyrylamino)-3-oxo-azepane-1-carboxylic acid benzyl ester
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]=[N+]=[N-])[CH:13]([OH:21])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]1([C:28](=[O:45])[CH2:29][CH:30]([CH2:34][S:35]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:37])=[O:36])[C:31](O)=[O:32])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:31](=[O:32])[CH:30]([CH2:34][S:35]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:37])=[O:36])[CH2:29][C:28]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:45])[C:13](=[O:21])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
3
Procedure
The crude 4-amino-3-hydroxy-azepane-1-carboxylic acid benzyl ester was coupled to 4-morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyric acid and oxidized, as described above, to yield 4-(4-morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyrylamino)-3-oxo-azepane-1-carboxylic acid benzyl ester; 1H NMR: (DMSO) 8.46–8.42 (m, 1H), 7.44–7.24 (m, 10H), 5.18–5.04 (m, 2H), 4.52–4.33 (m, 4H), 4.04–3.76 (m, 2H), 3.58–3.30 (m, 11H), 3.11–3.03 (m, 1H), 2.96–2.78 (m, 1H), 2.72–2.57 (m, 1H), 1.84–1.55 (m, 4H); MS: (M+H)+ 600.