Potassium Carbonate → HCID 178455609, compound

HRID 2294730Notes

Reaction equation

HRID 2294730 reaction equation
[C:1]([S:5]([CH2:8][C@@H:9]([CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:10]([NH:12][C@@H:13]([CH2:32][C:33]1[N:34]=[CH:35][N:36](C(OC(C)(C)C)=O)[CH:37]=1)[C:14]([NH:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]([OH:24])[C@H:19]([CH:21]1[CH2:23][CH2:22]1)[F:20])=[O:15])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CO>[C:1]([S:5]([CH2:8][C@@H:9]([CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:10]([NH:12][C@@H:13]([CH2:32][C:33]1[N:34]=[CH:35][NH:36][CH:37]=1)[C:14]([NH:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]([OH:24])[C@H:19]([CH:21]1[CH2:22][CH2:23]1)[F:20])=[O:15])=[O:11])(=[O:6])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 22879400HCID 22879400, compound

Product 1

HCID 178455609HCID 178455609, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 610 mg (0.8 mmol) of crude (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-3-fluoro-2-hydroxypropyl]-1-Boc-imidazole-4-propionamide and 110 mg (0.8 mmol) of potassium carbonate in 10 ml of methanol is stirred at room temperature under argon for 1 hour. Subsequently, 100 mg (1.9 mmol) of ammonium chloride are added. The mixture is stirred at room temperature for a further 15 minutes and thereafter evaporated under reduced pressure. The residue is dissolved in 20 ml of ethyl acetate and washed in succession with 10 ml of water and 10 ml of saturated sodium chloride solution. The aqueous phases are back-extracted twice with 20 ml of ethyl acetate. The pooled organic phases are dried over sodium sulphate and evaporated under reduced pressure. For purification, the residue (300 mg of a foam) is purified on 50 g of silica gel using a 9:1:0.1 mixture of methylene chloride, isopropanol and ammonia as the eluent. After lyophilization from dioxan there are obtained 95 mg of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-3-fluoro-2-hydroxypropyl]imidazole-4-propionamide as a colourless powder; MS: 633 (M+H)+.

Workup

  1. stirringThe mixture is stirred at room temperature for a further 15 minutes
  2. customevaporated under reduced pressure
  3. dissolutionThe residue is dissolved in 20 ml of ethyl acetate
  4. washwashed in succession with 10 ml of water and 10 ml of saturated sodium chloride solution
  5. extractionThe aqueous phases are back-extracted twice with 20 ml of ethyl acetate
  6. dry with materialThe pooled organic phases are dried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customFor purification
  9. customthe residue (300 mg of a foam) is purified on 50 g of silica gel using
  10. additiona 9:1:0.1 mixture of methylene chloride, isopropanol and ammonia as the eluent

Sources & evidence

ORD record
ord-e161ff0b448142a18080094b2e1a12f0
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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