Potassium Carbonate → HCID 178447082, compound

HRID 1197937Notes

Reaction equation

HRID 1197937 reaction equation
C1(C[C@H]([NH:15][C:16](=[O:49])[C@@H:17]([NH:31][C:32](=[O:48])[C@@H:33]([CH2:41][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:18][C:19]2[N:20](C(OC(C)(C)C)=O)[CH:21]=[N:22][CH:23]=2)C(O)C[N+]([O-])=O)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:44][C:43]([CH3:46])([CH3:45])[C:42](=[O:47])[CH2:41][C@@H:33]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:32]([NH:31][CH:17]([CH2:18][C:19]1[N:20]=[CH:21][NH:22][CH:23]=1)[C:16]([NH2:15])=[O:49])=[O:48]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 70064272HCID 70064272, compound

Product 1

HCID 178447082HCID 178447082, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In an analogous manner to that described in Example 4 by cleaving off the Boc protecting group from (S)-N-[(1S, 2RS)-1-(cyclohexylmethyl)-2-hydroxy-3-nitropropyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamamido]-3-t-butoxycarbonylimidazole-4-propionamide with potassium carbonate in methanol and subsequently purifying by chromatography on 50 g of silica gel using a 200:10:1 mixture of methylene chloride, methanol and ammonia as the eluting agent there were obtained the two epimeric compounds (S)-N-[(1S,2S or R)-1-(cyclohexylmethyl)-2-hydroxy-3-nitropropyl]-α-[(R)-α-(3 3-dimethyl-2-oxobutyl)hydrocinnamamido]imidazole-4-propionamide and (S)-N[(1S,2R or S)-1-(cyclohexylmethyl)-2-hydroxy-3-nitropropyl]-α-[(R)-α-(3.3-dimethyl-2-oxobutyl)hydrocinnamamido]imidazole-4-propionamide, in both cases as a foam, MS (each): 584 (M+H)+.

Workup

  1. customsubsequently purifying by chromatography on 50 g of silica gel using
  2. additiona 200:10:1 mixture of methylene chloride, methanol and ammonia as the eluting agent there

Sources & evidence

ORD record
ord-b0d7e3e29ca94557bc99b476f959d885
Source dataset
uspto-grants-1994_01
Patent number
US05278148

Reaction notes

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