Triethylamine → 2-(Benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate

HRID 451788노트

반응식

HRID 451788 반응식
[OH:1][CH2:2][CH:3]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:4][C:5]1([CH3:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH3:30][S:31]([O:1][CH2:2][CH:3]([NH:12][C:13]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:22])[CH2:4][C:5]1([CH3:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)(=[O:33])=[O:32]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59201634Benzyl 1-hydroxy-3-(1-methylcyclohexyl)propan-2-ylcarbamate

생성물 1

HCID 866394482-(Benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A mixture of 0.3607 g (1.18 mmol) of benzyl 1-hydroxy-3-(1-methylcyclohexyl)propan-2-ylcarbamate, 0.4 mL (2.87 mmol, 2.43 equiv) of triethylamine, 0.1 mL (1.29 mmol, 1.09 equiv) of methanesulfonyl chloride in CH2Cl2 (10 mL) was stirred at 0° C. for 1.5 h. The reaction mixture was quenched with ice water, extracted with CH2Cl2, washed with aqueous NaHCO3, and dried over Na2SO4. After the solvent was removed in vacuo, the crude 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate was used directly in the next step without further purification. MS ESI +ve m/z 406 (M+Na).

후처리

  1. customThe reaction mixture was quenched with ice water
  2. extractionextracted with CH2Cl2
  3. washwashed with aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. customAfter the solvent was removed in vacuo
  6. customthe crude 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propyl methanesulfonate was used directly in the next step without further purification

출처 및 근거

ORD 기록
ord-955a3d1e77ea42498895707e1b154213
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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