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Triethylamine → 3-Hydroxy-2-(2-trimethylsilanyl-ethoxycarbonylamino)-propionic Acid Methyl Ester

HRID 413616
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반응식

HRID 413616 반응식
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.[CH3:17][Si:18]([CH3:33])([CH3:32])[CH2:19][CH2:20][O:21][C:22](=O)[O:23]N1C(=O)CCC1=O>ClCCl>[CH3:2][O:3][C:4](=[O:9])[CH:5]([NH:6][C:22]([O:21][CH2:20][CH2:19][Si:18]([CH3:33])([CH3:32])[CH3:17])=[O:23])[CH2:7][OH:8]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate

생성물 1

HCID 540428173-Hydroxy-2-(2-trimethylsilanyl-ethoxycarbonylamino)-propionic Acid Methyl Ester수율 108.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 1.25 g serine methyl ester hydrochloride, 2.25 ml triethylamine and 10 ml dichloromethane was added at 0° C. a solution of 2.22 g carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-trimethylsilanyl-ethyl ester [R. E. Shute, D. H. Rich, Synthesis, 1987, 346]. After stirring for 24 h at rt the reaction mixture was washed two times with 1N potassium hydrogen sulfate, once with saturated sodium bicarbonate solution and once with brine. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 2.29 g of a colorless liquid.

후처리

  1. washwas washed two times with 1N potassium hydrogen sulfate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-32f4397a1e38411d81b70366178231fa
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06569411B2

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