Potassium Carbonate → HCID 178447082, compound

HRID 847303Notes

Reaction equation

HRID 847303 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[C:3](=[O:33])[CH2:4][C@@H:5]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:6]([NH:8][CH:9]([CH2:13][C:14]1[N:15](C(OC(C)(C)C)=O)[CH:16]=[N:17][CH:18]=1)[C:10]([NH2:12])=[O:11])=[O:7].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][C:2]([CH3:35])([CH3:34])[C:3](=[O:33])[CH2:4][C@@H:5]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:6]([NH:8][CH:9]([CH2:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1)[C:10]([NH2:12])=[O:11])=[O:7]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57161905HCID 57161905, compound

Product 1

HCID 178447082HCID 178447082, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

490 mg (0.565 mmol) of (S)-N-[(1S,2S,4S,5S or R)-1-(cyclohexylmethyl)-2,5-dihydroxy-6-[4-(2-hydroxyethyl)-1-piperazinyl]-4-isopropylhexyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamamido]-3-t-butoxycarbonylimidazole-4-propionamide are 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 is evaporated and the residue is chromatographed on 35 g of silica gel with a 110:10:1 mixture of methylene chloride, methanol and ammonia as the eluting agent, whereby there are obtained 347 mg of (S)-N-[(1S,2S,4S,5S or R)-1-(cyclohexylmethyl)-2,5-dihydroxy-6-[4-(2-hydroxyethyl)-1-piperazinyl]-4-isopropylhexyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamamido]imidazole-4-propionamide as a white foam, MS: 768 (M+H)+.

Workup

  1. customThereafter, the reaction mixture is evaporated
  2. customthe residue is chromatographed on 35 g of silica gel with a 110:10:1 mixture of methylene chloride, methanol and ammonia as the eluting agent, whereby there

Sources & evidence

ORD record
ord-241a7221af6e47f99523af4a2850c1e6
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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