Isopropanol → HCID 12051481, compound

HRID 1935418Notes

Reaction equation

HRID 1935418 reaction equation
[CH3:1][O:2][C@@H:3]([C@@H:10]([NH:15][C:16]([C@H:18]1[O:20][C@@H:19]1[C:21]([OH:23])=[O:22])=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:24][CH:25](O)[CH3:26].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][O:2][C@@H:3]([C@@H:10]([NH:15][C:16]([C@H:18]1[O:20][C@@H:19]1[C:21]([O:23][CH:25]([CH3:26])[CH3:24])=[O:22])=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 10868DicyclohexylcarbodiimideHCID 12051478HCID 12051478, compound

Product 1

HCID 12051481HCID 12051481, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of (2S,3S)-3-[[1-(S)-[α-(R)-methoxybenzyl]-3-methylbutyl]carbamoyl]oxirane-2-carboxylic acid (105 mg, 0.327 mmol), 2-propanol (30 μl, 0.40 mmol.) and 4-dimethylaminopyridine (8 mg, 0.07 mmol.) in anhydrous dichloromethane (4 mL) was added 1,3-dicyclohexylcarbodiimide (75 mg, 0.36 mmol.) under chilling with ice. The resulting mixture was stirred at 5° C. for 30 minutes, and then stirred overnight at room temperature. The mixture was placed under reduced pressure to distill off the solvent. The residue was mixed with ethyl acetate and 10% citric acid, and the insoluble material was removed by filtration. The filtrate was successively washed with water, aqueous saturated sodium hydrogen carbonate solution, and aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by middle pressure silica gel column chromatography (n-hexane/ethyl acetate=3/1), to give the titled compound as a white crystalline product (70 mg, yield: 59%).

Workup

  1. temperatureunder chilling with ice
  2. stirringstirred overnight at room temperature
  3. distillationto distill off the solvent
  4. additionThe residue was mixed with ethyl acetate and 10% citric acid
  5. customthe insoluble material was removed by filtration
  6. washThe filtrate was successively washed with water, aqueous saturated sodium hydrogen carbonate solution, and aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by middle pressure silica gel column chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-c9757d8afdca4aa8aad1fdf908891cc2
Source dataset
uspto-grants-2002_05
Patent number
US06387908B1

Reaction notes

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