N-[(S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamoyl]-3-(2,4-dinitrophenyl)-L-histidine → HCID 178455618, compound
Reaction equation
[NH2:1][C@@H:2]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C@@H:3]([OH:11])[CH:4]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[OH:5].[C:19]([S:23]([CH2:26][C@@H:27]([CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:28]([NH:30][C@H:31]([C:50](O)=[O:51])[CH2:32][C:33]1[N:37](C2C=CC([N+]([O-])=O)=CC=2[N+]([O-])=O)[CH:36]=[N:35][CH:34]=1)=[O:29])(=[O:25])=[O:24])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([S:23]([CH2:26][C@@H:27]([CH2:53][C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[C:28]([NH:30][C@@H:31]([CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)[C:50]([NH:1][C@@H:2]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C@@H:3]([OH:11])[CH:4]([OH:5])[C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)=[O:51])=[O:29])(=[O:25])=[O:24])([CH3:22])([CH3:20])[CH3:21]Participants
3
Procedure
In an analogous manner to that described in Example 13, by reacting (1RS,2R,3S)-3-amino-4-cyclohexyl-1-(2-furyl)-1,2-butanediol with N-[(S)-α-[(t-butylsulphonyl)methyl]hydrocinnamoyl]-3-(2,4-dinitrophenyl)-L-histidine there was obtained (S)-α-[(S)-α-[(t-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3RS)-1-(cyclohexylmethyl)-2,3-dihydroxy-3-(2-furyl)propyl]imidazole-4-propionamide (1:1 mixture of epimers) as a pale yellow solid, MS: 657 (M+H)+. The more polar epimer, (S)-α-[(S)-α-[(t-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3R or S)-1-(cyclohexylmethyl)-2,3-dihydroxy-3-(2-furyl)propyl]imidazole-4-Propionamide, MS: 657 (M+H) can be separated from the above mixture by chromatography.
Sources & evidence
- ORD record
- ord-cbda038bc7e348cd9c9f8d2e58fb4aa2
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05134123
Reaction notes
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