(alphaRS,S)-alpha-benzyl-1-t-butoxycarbonyl-gamma-oxo-2-pyrrolidinebutyric acid → HCID 178456010, compound
Reaction equation
[CH2:1]([CH:8]([CH2:12][C:13](=[O:26])[C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C@@H:28]([CH2:49][C:50]1[N:51]=[CH:52][NH:53][CH:54]=1)[C:29]([NH:31][C@@H:32]([CH2:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1)[C@@H:33]([OH:41])[CH2:34][C@@H:35]([CH:38]([CH3:40])[CH3:39])[CH:36]=[CH2:37])=[O:30]>>[CH:43]1([CH2:42][C@H:32]([NH:31][C:29]([C@@H:28]([NH:27][C:9]([C@H:8]([CH2:12][C:13]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:26])[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:11])[CH2:49][C:50]2[N:51]=[CH:52][NH:53][CH:54]=2)=[O:30])[C@@H:33]([OH:41])[CH2:34][C@@H:35]([CH:38]([CH3:40])[CH3:39])[CH:36]=[CH2:37])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]1Participants
3
Procedure
In a manner analogous to that described in Example 27, by condensing (αRS,S)-α-benzyl-1-t-butoxycarbonyl-γ-oxo-2-pyrrolidinebutyric acid with (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide and subsequent epimer separation by chromatography, there were obtained t-butyl (S)-2-[[(S)-α-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]acetyl]-1-pyrrolidinecarboxylate (less polar isomer) and t-butyl (S)-2-[[(R)-γ-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]acetyl]-1-pyrrolidinecarboxylate. MS: 734 (M+H)+
Sources & evidence
- ORD record
- ord-ae69f54651654c3f8c1e50be2665627b
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05250517
Reaction notes
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