(2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester → (3S,5RS)-1-(4-amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one

HRID 1432930ノート

反応式

HRID 1432930 の反応式
C(OC([N:11]1[CH:16]([CH3:17])[CH2:15][N:14]([CH2:18][C:19]2[CH:28]=[C:27]3[C:22]([C:23]([NH2:29])=[N:24][CH:25]=[N:26]3)=[CH:21][CH:20]=2)[C:13](=[O:30])[C@@H:12]1[CH3:31])=O)C1C=CC=CC=1.[H][H]>[Pd].CO.C(O)(=O)C>[NH2:29][C:23]1[C:22]2[C:27](=[CH:28][C:19]([CH2:18][N:14]3[CH2:15][CH:16]([CH3:17])[NH:11][C@@H:12]([CH3:31])[C:13]3=[O:30])=[CH:20][CH:21]=2)[N:26]=[CH:25][N:24]=1

参加物

6

反応物 2

HCID 57166330(2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl esterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 57054033(3S,5RS)-1-(4-amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one収率 153.9%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

Palladium on carbon (10%, 700 mg) is added to a solution of (2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (1.62 g, 3.87 mmol) in 20 mL of methanol and 2 mL of acetic acid. The reaction mixture is left to stir in an atmosphere of hydrogen for eight hours. The palladium is filtered off, and the volitale solvents are removed on the rotovap. The crude product (1.7 g, 95%) is isolated as a white solid. The two epimers are separated on silica gel (1% triethylamine/15% methanol/methylene chloride). The minor epimer is assigned as (3S,5R)-1-(4-amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one and the major epimer is assigned as (3S,5S)-1-(4-amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one.

後処理

  1. waitThe reaction mixture is left
  2. filtrationThe palladium is filtered off
  3. customthe volitale solvents are removed on the rotovap

出典と根拠

ORDレコード
ord-1e8bf22d43164199bb126c50f2b7e6cc
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

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