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Benzyl chloroformate → (S)-2-[Benzyloxycarbonyl-(2,2-dimethoxy-ethyl)-amino]-propionic acid methyl ester

HRID 655539
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반응식

HRID 655539 반응식
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][O:13][C:14](=[O:24])[C@@H:15]([NH:17][CH2:18][CH:19]([O:22][CH3:23])[O:20][CH3:21])[CH3:16].C(=O)([O-])O.[Na+]>CC(C)=O.O>[CH3:12][O:13][C:14](=[O:24])[C@@H:15]([N:17]([C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])[CH2:18][CH:19]([O:22][CH3:23])[O:20][CH3:21])[CH3:16]
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참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 63697235(S)-2-(2,2-dimethoxy-ethylamino)-propionic acid methyl ester

생성물 1

HCID 67074039(S)-2-[Benzyloxycarbonyl-(2,2-dimethoxy-ethyl)-amino]-propionic acid methyl ester수율 72.4%

시약·촉매·용매 2

HCID 180Acetone용매
HCID 962
Water
용매

실험 절차

Benzyl chloroformate (4.46 g, 24.8 mmol) was added at 0° C. to a mixture of (S)-2-(2,2-dimethoxy-ethylamino)-propionic acid methyl ester (4.75 g, 24.8 mmol) and sodium hydrogencarbonate (4.17 g, 49.7 mmol) in acetone (25 mL) and water (25 mL). The ice bath was removed, then after 2 h the reaction mixture was poured onto ice water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient afforded the title compound (5.84 g, 72%). Yellow oil, MS (ISP)=348.2 (M+Na)+.

후처리

  1. customThe ice bath was removed
  2. additionafter 2 h the reaction mixture was poured onto ice water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-785dfeeb700248158c08923df641c2a0
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08071586B2

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