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

HRID 451788ノート

反応式

HRID 451788 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-955a3d1e77ea42498895707e1b154213
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

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