HCID 178431645, compound → HCID 178455619, compound

HRID 2294736Notes

Reaction equation

HRID 2294736 reaction equation
[C:1]([S:5]([CH2:8][C@@H:9]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:10]([NH:12][C@@H:13]([CH2:36][C:37]1[N:38]=[CH:39][NH:40][CH:41]=1)[C:14]([NH:16][C@H:17]([C@@H:26]1[C@H:30]([CH:31]2[CH2:33][CH2:32]2)[O:29]C(C)(C)[O:27]1)[CH2:18][CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1)=[O:15])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2]>CO.Cl>[C:1]([S:5]([CH2:8][C@@H:9]([CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:10]([NH:12][C@@H:13]([CH2:36][C:37]1[N:38]=[CH:39][NH:40][CH:41]=1)[C:14]([NH:16][C@@H:17]([CH2:18][CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1)[C@@H:26]([OH:27])[C@H:30]([CH:31]1[CH2:32][CH2:33]1)[OH:29])=[O:15])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 178431645HCID 178431645, compound

Product 1

HCID 178455619HCID 178455619, compoundYield 6.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 90 mg (0.3 mmol) of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(S)-1-[(4R,5S)-5-cyclopropyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(4-oxocyclohexyl)ethyl]imidazole-4-propionamide in 1 ml of methanol and 1 ml of 2N hydrochloric acid is stirred at room temperature for 3 hours. Subsequently, the reaction solution is evaporated and, for purification, the residue is chromatographed on 20 g of silica gel using a 14:1:0.1 mixture of methylene chloride, methanol and ammonia as the eluent. There are obtained 13 mg of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-3-cyclopropyl-2,3-dihydroxy-1-[(4-oxocyclohexyl)methyl]propyl]imidazole-4-propionamide as a colourless solid; MS: 684 (M+H)+.

Workup

  1. customSubsequently, the reaction solution is evaporated and, for purification
  2. customthe residue is chromatographed on 20 g of silica gel using
  3. additiona 14:1:0.1 mixture of methylene chloride, methanol and ammonia as the eluent

Sources & evidence

ORD record
ord-1c763452eb784446a0deab2fb10fe344
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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