Triethylamine → Methanesulfonic acid (S)-2-tert-butoxycarbonylamino-4,4-dimethyl-pentyl ester

HRID 1052133ノート

反応式

HRID 1052133 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]([CH2:14][OH:15])[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][C@@H:8]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:14][O:15][S:24]([CH3:27])(=[O:26])=[O:25])=[O:16])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58280489((S)-1-hydroxymethyl-3,3-dimethyl-butyl)-carbamic acid tert-butyl ester

生成物 1

HCID 118151399Methanesulfonic acid (S)-2-tert-butoxycarbonylamino-4,4-dimethyl-pentyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of ((S)-1-hydroxymethyl-3,3-dimethyl-butyl)-carbamic acid tert-butyl ester (250 mg, 0.756 mmol) and triethylamine (0.116 mL, 0.832 mmol) in CH2Cl2 (4 mL) cooled at −10° C. was added under nitrogen atmosphere mesylchloride (0.065 mL, 0.832 mmol) and the reaction mixture was stirred at 0° C. for 1.5 h. The reaction mixture was quenched with ice and water then extracted twice with EtOAc. The combined organic layers were washed with water, dried (Na2SO4), filtered and concentrated. The crude material (colorless oil) was used without purification in the next step. TLC, Rf (c-hexane/EtOAc 1:1): 0.46.

後処理

  1. customThe reaction mixture was quenched with ice and water
  2. extractionthen extracted twice with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material (colorless oil) was used without purification in the next step

出典と根拠

ORDレコード
ord-00bee42ab69b492c8fde03c83b3525ca
出典データセット
uspto-grants-2016_07
特許番号
US09388199B2

反応ノート

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