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

HRID 595167노트

반응식

HRID 595167 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-28b01ec3569a49af8748445519917d4d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242984B2

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