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

HRID 1432905

反応式

HRID 1432905 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-d0c248c53bfe4d62a63af17d0d0d2e4c
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

関連ノート

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