Phosgene → 1-{4'-[4-(3-Benzyl-2-oxo-oxazolidin-5-yl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

HRID 1183317노트

반응식

HRID 1183317 반응식
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]([OH:37])[CH2:28][NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:45](Cl)(Cl)=[O:46].CCOC(C)=O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]4[O:37][C:45](=[O:46])[N:29]([CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:28]4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 6371Phosgene2회HCID 8471Triethylamine2회HCID 8857Ethyl AcetateHCID 665773521-{4'-[4-(2-Benzylamino-1-hydroxy-ethyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

생성물 1

HCID 665777731-{4'-[4-(3-Benzyl-2-oxo-oxazolidin-5-yl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

1-{4′-[4-(2-Benzylamino-1-hydroxy-ethyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.190 g, 0.38 mmol) was dissolved in toluene (4 mL) then placed under N2 atmosphere at 0° C. Triethylamine (0.159 mL, 1.14 mmol) and phosgene (1.9M in toluene, 0.201 mL, 0.38 mmol) were added and the reaction stirred at 0° C. After two hours an additional portion of each of triethylamine (0.160 mL) and phosgene (0.200 mL) were added and the reaction stirred an additional 20 minutes. The reaction was submitted to standard workup procedures and silica gel chromatography (0-40% EtOAc in hexanes) to yield the title compound.

후처리

  1. customthen placed under N2 atmosphere at 0° C
  2. stirringthe reaction stirred an additional 20 minutes

출처 및 근거

ORD 기록
ord-29a098f6d46e4a59b76f6643c648f7cc
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664220B2

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