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Triethylamine → 2-{1-[(Tert-butoxycarbonyl)amino]cyclopropyl}ethyl methanesulfonate

HRID 1786161
ノート
印刷プレビュー

反応式

HRID 1786161 の反応式
[OH:1][CH2:2][CH2:3][C:4]1([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5]1.C(N(CC)CC)C.[S:22](Cl)([CH3:25])(=[O:24])=[O:23]>ClCCl>[CH3:25][S:22]([O:1][CH2:2][CH2:3][C:4]1([NH:7][C:8]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:14])[CH2:5][CH2:6]1)(=[O:24])=[O:23]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 129931391,1-Dimethylethyl N-[1-(2-hydroxyethyl)cyclopropyl]carbamate

生成物 1

HCID 129931402-{1-[(Tert-butoxycarbonyl)amino]cyclopropyl}ethyl methanesulfonate収率 87%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-20 °C

実験手順

To a solution of 6.472 g (32.16 mmol) of tert-butyl 1-(2-hydroxyethyl)cyclopropylcarbamate in 61 ml of anhydrous dichloromethane was added 12.79 ml (91 mmol) of anhydrous triethylamine. The resulting mixture is cooled at −20° C. Then 3.54 ml (45.66 mmol) of mesyl chloride in 11 ml of anhydrous dichloromethane was added. The resulting mixture was stirred at room temperature for 2 h. The mixture was poured into ice-water and the organic layer was washed with saturated aqueous sodium chloride, dried over sodium sulfate and evaporated. The crude product was triturated with petroleum ether and filtered to give 7.82 g of pure product as an orange solid. Mp: 88-89° C.

後処理

  1. washthe organic layer was washed with saturated aqueous sodium chloride
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe crude product was triturated with petroleum ether
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-0187f9bd4d8442db85d80f59adc4af0b
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07507743B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート