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Triethylamine → (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl methanesulfonate

HRID 44636
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HRID 44636 반응식
[OH:1][CH2:2][C@@H:3]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[S:25](Cl)([CH3:28])(=[O:27])=[O:26].[O-]S([O-])(=O)=O.[Na+].[Na+]>ClCCl.O>[CH3:28][S:25]([O:1][CH2:2][C@@H:3]([NH:10][C:11]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:27])=[O:26]
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 24436Sodium SulfateHCID 31297Methanesulfonyl chlorideHCID 7016462(S)-2-((N-tert-Butoxycarbonyl)amino)-2-phenylethanol

생성물 1

HCID 10335849(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl methanesulfonate수율 98%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6344Dichloromethane용매

실험 절차

The solution of 68.9 g (0.29 mol) of tert-butyl (1S)-2-hydroxy-1-phenylethylcarbamate and triethylamine (40.36 mL, 0.29 mol) in 700 mL of dry dichloromethane under inert atmosphere was cooled to −10° C. and 24.79 mL (0.319 mol) of mesylchloride were added dropwise. After 2 hours at 0° C. the mixture was poured into ice and water and extracted with dichloromethane. The organic phase was washed with diluted HCl, aqueous NaHCO3, brine and dried over Na2SO4 yielding 89.8 g of the product (98% yield).

후처리

  1. extractionextracted with dichloromethane
  2. washThe organic phase was washed with diluted HCl, aqueous NaHCO3, brine

출처 및 근거

ORD 기록
ord-13200e85ff694201877cc88e63376806
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541429B2

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