Triphenyl Phosphate → (3S, 5R)-1-(2,4-dimethoxy-benzyl)-3,5-dimethyl-4-trifluoroacetyl-piperazin-2-one

HRID 1432905

반응식

HRID 1432905 반응식
[CH3:1][O:2][C:3]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:4]=1[CH2:5][N:6]([CH2:18][C@@H:19](O)[CH3:20])[C:7](=[O:17])[C@@H:8]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH3:9].C1(OP(OC2C=CC=CC=2)(OC2C=CC=CC=2)=O)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:4]=1[CH2:5][N:6]1[CH2:18][C@@H:19]([CH3:20])[N:10]([C:11](=[O:16])[C:12]([F:14])([F:13])[F:15])[C@@H:8]([CH3:9])[C:7]1=[O:17]

참가 물질

5

반응물 3

HCID 8289Triphenyl PhosphateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86592544(2S, 2S)-N-(2,4-Dimethoxy-benzyl)-N-(2-hydroxypropyl)-2-(2,2,2-trifluoroacetylamino)-propionamide

생성물 1

HCID 57171471(3S, 5R)-1-(2,4-dimethoxy-benzyl)-3,5-dimethyl-4-trifluoroacetyl-piperazin-2-one수율 43.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(2S, 2S)-N-(2,4-Dimethoxy-benzyl)-N-(2-hydroxypropyl)-2-(2,2,2-trifluoroacetylamino)-propionamide (3.64 g, 9.29 mmol) is dissolved in 25 mL of tetrahydrofuran. Triphenylphosphate (3.65 g, 14.0 mmol) is added, and the resulting mixture is cooled to 0° C. before diethyl azodicarboxylate (2.2 mL, 14 mmol) is added slowly. The resulting mixture is left to stir overnight. The reaction mixture is condensed, and the residue is purified by column chromatography (SiO2, 25% ethyl acetate/hexane). The desired product, (3S, 5R)-1-(2,4-dimethoxy-benzyl)-3,5-dimethyl-4-trifluoroacetyl-piperazin-2-one (1.5 g, 43% yield), is isolated as a clear oil.

후처리

  1. additionis added slowly
  2. waitThe resulting mixture is left
  3. customcondensed
  4. customthe residue is purified by column chromatography (SiO2, 25% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-d0c248c53bfe4d62a63af17d0d0d2e4c
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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