Methyl chloroformate → (S)-benzyl 4-(difluoromethoxy)-2-(methoxycarbonylamino)butanoate

HRID 71968노트

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HRID 71968 반응식
[NH2:1][C@@H:2]([CH2:13][CH2:14][O:15][CH:16]([F:18])[F:17])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH3:19][O:20][C:21](Cl)=[O:22]>ClCCl>[F:18][CH:16]([F:17])[O:15][CH2:14][CH2:13][C@H:2]([NH:1][C:21]([O:20][CH3:19])=[O:22])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

참가 물질

4

반응물 2

HCID 6586Methyl chloroformateHCID 67991507(S)-benzyl 2-amino-4-(difluoromethoxy)butanoate

생성물 1

HCID 59610623(S)-benzyl 4-(difluoromethoxy)-2-(methoxycarbonylamino)butanoate수율 40%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

(S)-Benzyl 2-amino-4-(difluoromethoxy)butanoate (116 mg, 0.448 mmol) was dissolved in anhydrous dichloromethane (2.5 mL) and cooled down to 0° C. and TEA (181 mg, 1.79 mmol) and methylchloroformate (51 mg, 0.538 mmol) were added respectively. The mixture was stirred for 30 minutes and then it was stirred at room temperature overnight. The resulting product mixture was quenched with saturated NaHCO3 and extracted with dichloromethane. The organic layer was washed with saturated NH4Cl solution and brine and dried over Na2SO4. The volatiles were removed in vacuo to afford 56 mg (40%) of desired product after column purification.

후처리

  1. stirringit was stirred at room temperature overnight
  2. customThe resulting product mixture was quenched with saturated NaHCO3
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with saturated NH4Cl solution and brine
  5. dry with materialdried over Na2SO4
  6. customThe volatiles were removed in vacuo

출처 및 근거

ORD 기록
ord-15fc59ba3d8a4f63b4d53ffa27a5136b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822430B2

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