Water → 2-{(S)-2-[4-(4-methoxy-3-methyl-phenyl)-2,5-dioxo-imidazolidin-1-yl]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester

HRID 2222985노트

반응식

HRID 2222985 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:34])[C@@H:12]([NH:20][C:21](=[O:33])[CH:22]([NH2:32])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([CH3:31])[CH:24]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4].C(N(C(C)C)CC)(C)C.[O:44]=[C:45](Cl)OC(Cl)(Cl)Cl.O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:34])[C@@H:12]([N:20]2[C:21](=[O:33])[CH:22]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([CH3:31])[CH:24]=3)[NH:32][C:45]2=[O:44])[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[S:8][CH:9]=1)=[O:4]

참가 물질

6

반응물 4

HCID 962WaterHCID 10426DiphosgeneHCID 81531DiisopropylethylamineHCID 866040592-{(S)-2-[2-amino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester

생성물 1

HCID 586154922-{(S)-2-[4-(4-methoxy-3-methyl-phenyl)-2,5-dioxo-imidazolidin-1-yl]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-10 °C

실험 절차

A solution of 2-{(S)-2-[2-amino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester (0.40 g , 0.83 mmol) and diisopropylethylamine (0.72 mL, 4.14 mmol) in dichloromethane (20 mL) was added to a solution of diphosgene (0.07 mL, 0.58 mmol) in dichloromethane (20 mL) at −10° C. The mixture was stirred at −10° C. for 0.5 hours. Water was added to quench the reaction, then the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography over silica gel eluted with ethyl acetate to give 2-{(S)-2-[4-(4-methoxy-3-methyl-phenyl)-2,5-dioxo-imidazolidin-1-yl]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester as an off white foam (0.29 g, 69%).

후처리

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography over silica gel
  9. washeluted with ethyl acetate

출처 및 근거

ORD 기록
ord-99891ee4d8fc4786b80b586df3ed17fb
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371869B2

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