Potassium Carbonate → HCID 178447083, compound

HRID 1197926Notes

Reaction equation

HRID 1197926 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:18][C:19](=[O:52])[C@@H:20]([NH:34][C:35](=[O:51])[C@@H:36]([CH2:44][C:45](=[O:50])[C:46]([CH3:49])([CH3:48])[CH3:47])[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:21][C:22]2[N:23](C(OC(C)(C)C)=O)[CH:24]=[N:25][CH:26]=2)[C@@H:9]([OH:17])[CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([CH2:7][C@H:8]([NH:18][C:19](=[O:52])[C@@H:20]([NH:34][C:35](=[O:51])[C@@H:36]([CH2:44][C:45](=[O:50])[C:46]([CH3:48])([CH3:49])[CH3:47])[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:21][C:22]2[N:23]=[CH:24][NH:25][CH:26]=2)[C@@H:9]([OH:17])[CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22849831HCID 22849831, compound

Product 1

HCID 178447083HCID 178447083, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

408 mg (0.565 mmol) of (S)-N-[(1S,2S)-1-(cyclohexyl methyl)-2-hydroxy-3-(2-oxo-1-pyrrolidinyl)propyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamamido]-3-t-butoxycarbonylimidazole-4-propionamide were dissolved in 5.5 ml of methanol, treated with 23 mg of potassium carbonate and stirred at room temperature for 5 hours. Thereafter, the reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride extracts were dried over potassium carbonate and evaporated, and the residue was chromatographed on 35 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent, whereby there were obtained 280 mg (80%) of (S)-N-[(1S,2S)-1-(cyclohexylmethyl)-2-hydroxy-3-(2-oxo-1-pyrrolidinyl)propyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamamido]-imidazole-4-propionamide as an amorphous solid, MS: 622 (M+H)+.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe methylene chloride extracts were dried over potassium carbonate
  3. customevaporated
  4. customthe residue was chromatographed on 35 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent

Sources & evidence

ORD record
ord-28cb247b63814ed99eb73fb35503bc52
Source dataset
uspto-grants-1994_01
Patent number
US05278148

Reaction notes

Loading…