(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol → HCID 22879395, compound

HRID 2294693Notes

Reaction equation

HRID 2294693 reaction equation
[C:1]([S:5]([CH2:8][C@@H:9]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:10]([NH:12][C@H:13]([C:32](O)=[O:33])[CH2:14][C:15]1[N:19]=[CH:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=2[N+:29]([O-:31])=[O:30])[CH:16]=1)=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[NH2:42][C@@H:43]([CH2:51][CH:52]1[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1)[C@@H:44]([OH:50])[C@H:45]([CH:47]1[CH2:49][CH2:48]1)[OH:46]>>[C:1]([S:5]([CH2:8][C@@H:9]([CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:10]([NH:12][C@@H:13]([CH2:14][C:15]1[N:19]=[CH:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=2[N+:29]([O-:31])=[O:30])[CH:16]=1)[C:32]([NH:42][C@@H:43]([CH2:51][CH:52]1[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1)[C@@H:44]([OH:50])[C@H:45]([CH:47]1[CH2:49][CH2:48]1)[OH:46])=[O:33])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 14930738(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediolHCID 15126588HCID 15126588, compound

Product 1

HCID 22879395HCID 22879395, compound

Procedure

In an analogous manner to that described in Example 4, by condensing N-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamoyl]-1-(2,4-dinitrophenyl)-L-histidine with (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol there is obtained (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-1-(2,4-dinitrophenyl)imidazole-4-propionamide as a yellow solid; MS: 797 (M+H)+.

Sources & evidence

ORD record
ord-60cdeb8964f040ffbe2c4588a1f564e9
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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