Water → 4-(2-t-Butoxycarbonylaminoethyl)phenoxymethyl phosphonic acid, diethyl ester

HRID 1527노트

반응식

HRID 1527 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:13])[OH:12])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:16]([O:18][P:19]([CH2:24]OS(C1C=CC(Cl)=CC=1)(=O)=O)(=[O:23])[O:20][CH2:21][CH3:22])[CH3:17].O>CS(C)=O>[C:5]([O:13][C:11]([NH:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:24][P:19](=[O:23])([O:18][CH2:16][CH3:17])[O:20][CH2:21][CH3:22])=[CH:7][CH:6]=1)=[O:12])([CH3:8])([CH3:6])[CH3:4]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 9974693HCID 9974693, 화합물HCID 204361692-(4-Hydroxyphenyl)ethylcarbamic acid

생성물 1

HCID 867521914-(2-t-Butoxycarbonylaminoethyl)phenoxymethyl phosphonic acid, diethyl ester

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

A solution of 2-(4-hydroxyphenyl)ethylcarbamic acid, t-butyl ester1 (4.0 g, 16.9 mMol) in dry DMSO (37.5 ml) was cooled in an ice-bath and treated with sodium hydride (80% in mineral oil 0.557 g, 1.1 equiv) with stirring under argon according to the method described by Cornforth2. When effervescence ceased a solution of 4-chlorobenzenesulfonyloxymethylphosphonate diethyl ester (6.07 g, 1.05 equiv) in dry DMSO (110 ml) was added and the resulting pale yellow solution stirred at room temperature overnight. The mixture was then poured into water (550 ml) and extracted with diethyl ether/ethyl acetate (1:1, 3×150 ml) and finally ethyl acetate (3×100 ml). The combined extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated to dryness. The resulting oil was purified by chromatography on silica gel with a gradient of 3:2 pentane:ethyl acetate rising to 100% ethyl acetate to give the title compound as a colourless viscous oil.

후처리

  1. additionwas added
  2. stirringthe resulting pale yellow solution stirred at room temperature overnight
  3. extractionextracted with diethyl ether/ethyl acetate (1:1, 3×150 ml) and finally ethyl acetate (3×100 ml)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe resulting oil was purified by chromatography on silica gel with a gradient of 3:2 pentane

출처 및 근거

ORD 기록
ord-5e96551488e842a0ae7a5944f04ecff0
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726165

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