Potassium Carbonate → HCID 178455612, compound

HRID 2294702Notes

Reaction equation

HRID 2294702 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)[OH: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)[OH:20])=[O:15])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 22879396HCID 22879396, compound

Product 1

HCID 178455612HCID 178455612, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.82 g (about 3.8 mmol) of crude (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-1-Boc-imidazole-4-propionamide and 0.35 g (2.55 mmol) of potassium carbonate in 20 ml of methanol is stirred at room temperature under argon for 1 hour. Thereafter, 0.33 g (6.1 mmol) of ammonium chloride is added and the mixture is stirred at room temperature for a further 15 minutes. The reaction mixture is subsequently evaporated under reduced pressure, the residue is taken up in 60 ml of ethyl acetate and this solution is washed in succession with 30 ml of water and 30 ml of saturated sodium chloride solution. The aqueous phases are back-extracted twice with 60 ml of ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated under reduced pressure. The residue is triturated in 15 ml of ether, then filtered off under suction and, for further purification, chromatographed on 150 g of silica gel using a 4:1:0.1 mixture of methylene chloride, methanol and ammonia as the eluent. There are obtained 1.13 g of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-imidazole-4-propionamide as a colourless solid; MS: 631 (M+H)+.

Workup

  1. customThe reaction mixture is subsequently evaporated under reduced pressure
  2. washthis solution is washed in succession with 30 ml of water and 30 ml of saturated sodium chloride solution
  3. extractionThe aqueous phases are back-extracted twice with 60 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customThe residue is triturated in 15 ml of ether
  7. filtrationfiltered off under suction and, for further purification
  8. customchromatographed on 150 g of silica gel using
  9. additiona 4:1:0.1 mixture of methylene chloride, methanol and ammonia as the eluent

Sources & evidence

ORD record
ord-7be6e72ada584d06a551f46dc75aed14
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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