Triethylamine → Methanesulfonic acid 2-tert-butoxycarbonylamino-2-methyl-propyl ester

HRID 595167ノート

反応式

HRID 595167 の反応式
C(N(CC)CC)C.[OH:8][CH2:9][C:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:12])[CH3:11].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([O:8][CH2:9][C:10]([NH:13][C:14]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:20])([CH3:11])[CH3:12])(=[O:24])=[O:23]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

生成物 1

HCID 11659022Methanesulfonic acid 2-tert-butoxycarbonylamino-2-methyl-propyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Dichloromethane (50 mL) and triethylamine (9.72 ml, 69.7 mmol) were added to a flask containing tert-butyl (1-hydroxy-2-methylpropan-2-yl)carbamate (3.30 g, 17.4 mmol). The reaction mixture was stirred and then chilled to 0° C. for 10 minutes. Methanesulfonyl chloride (2.72 ml, 34.9 mmol) was dissolved in dichloromethane (15 mL) and slowly added to the reaction mixture, which was then allowed to stir at 0° C. for 2 hours. The reaction was quenched with saturated aqueous sodium bicarbonate solution and the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford 2-((tert-butoxycarbonyl)amino)-2-methylpropyl methanesulfonate. 1H NMR (500 MHz, DMSO-d6): δ 6.73 (s, 1H), 4.20 (s, 2H), 3.12 (s, 3H), 1.36 (s, 9H), 1.17 (s, 6H).

後処理

  1. additionslowly added to the reaction mixture, which
  2. stirringto stir at 0° C. for 2 hours
  3. customThe reaction was quenched with saturated aqueous sodium bicarbonate solution
  4. customthe organic layer was separated
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-28b01ec3569a49af8748445519917d4d
出典データセット
uspto-grants-2016_01
特許番号
US09242984B2

反応ノート

読み込み中…