Methanesulfonyl chloride → 2-(Tert-butoxycarbonyl(prop-2-ynyl)amino)ethyl methanesulfonate

HRID 1971674ノート

反応式

HRID 1971674 の反応式
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][C:13]#[CH:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(N(CC)CC)C.CCOCC>[CH3:15][S:16]([O:1][CH2:2][CH2:3][N:4]([C:5]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:11])[CH2:12][C:13]#[CH:14])(=[O:18])=[O:17]

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 11672867tert-Butyl (2-hydroxyethyl)(prop-2-yn-1-yl)carbamate

生成物 1

HCID 581248922-(Tert-butoxycarbonyl(prop-2-ynyl)amino)ethyl methanesulfonate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8471Triethylamine溶媒

実験手順

A solution of 700 mg of 10d in 1 ml of triethyl amine and 15 ml of ether was treated at 0° C. with 320 μl of methanesulfonyl chloride in 3 ml of ether. The reaction mixture was stirred for ½ h and then quenched by addition of 20 ml of water and the product was extracted into ether. The organic extract was washed with 1M aq. K2CO3 and once with water, dried and concentrated, to give 900 mg of 10e as a colorless oil, essentially pure according to TLC and NMR, which was used without further purification in the next step. Rf 0.40 (heptane/ethyl acetate 1/1).

後処理

  1. customquenched by addition of 20 ml of water
  2. extractionthe product was extracted into ether
  3. extractionThe organic extract
  4. washwas washed with 1M aq. K2CO3 and once with water
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-15c7c6bf6316462bb235325e681b047c
出典データセット
uspto-grants-2013_04
特許番号
US08431564B2

反応ノート

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