Potassium Carbonate → HCID 86751644, compound

HRID 2294704Notes

Reaction equation

HRID 2294704 reaction equation
[C:1]([S:5]([CH2:8][C@@H:9]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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[CH2:23][CH2:22]1)[OH:20])=[O:15])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+].[C:69]([O:75][CH2:76]Cl)(=[O:74])[C:70]([CH3:73])([CH3:72])[CH3:71]>C(OCC)(=O)C>[C:69]([O:75][CH2:76][N:36]1[CH:37]=[C:33]([CH2:32][C@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([CH2:8][S:5]([C:1]([CH3:4])([CH3:2])[CH3:3])(=[O:7])=[O:6])[CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:14](=[O:15])[NH:16][C@@H:17]([CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C@@H:18]([OH:24])[C@H:19]([CH:21]2[CH2:22][CH2:23]2)[OH:20])[N:34]=[CH:35]1)(=[O:74])[C:70]([CH3:73])([CH3:72])[CH3:71]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 87885Chloromethyl pivalateHCID 178455612HCID 178455612, compound

Product 1

HCID 86751644HCID 86751644, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 250 mg (0.4 mmol) of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]imidazole-4-propionamide, 60 mg of 18-crown-6, 250 mg of potassium carbonate and 2 ml of chloromethyl pivalate is stirred at room temperature overnight. Thereafter, the reaction mixture is taken up in ethyl acetate and the ethyl acetate solution is washed with saturated ammonium chloride solution. After drying over sodium sulphate the solution is evaporated under reduced pressure and subsequently, for purification, the crude product obtained (1.3 g) is chromatographed on 120 g of silica gel using a 200:10:1 mixture of methylene chloride, methanol and ammonia as the eluent. There are obtained 145 mg of [4-[(S)-2-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-2-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]ethyl]imidazol-1-yl]methyl pivalate as a colourless solid; MS: 745 (M+H)+.

Workup

  1. washthe ethyl acetate solution is washed with saturated ammonium chloride solution
  2. dry with materialAfter drying over sodium sulphate the solution
  3. customis evaporated under reduced pressure
  4. customsubsequently, for purification
  5. customthe crude product obtained (1.3 g)
  6. customis chromatographed on 120 g of silica gel using
  7. additiona 200:10:1 mixture of methylene chloride, methanol and ammonia as the eluent

Sources & evidence

ORD record
ord-a1e72b7df05f47578cc1c33b5d01325e
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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