acetyl-DL-leucine → HCID 178474741、化合物

HRID 1106115

反応式

HRID 1106115 の反応式
[C:1]([NH:4][CH:5]([C:10]([OH:12])=O)[CH2:6][CH:7]([CH3:9])[CH3:8])(=[O:3])[CH3:2].ClC(OCC(C)C)=O.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:33]=[C:32]([OH:34])[C:31]([C:35]([OH:37])=[O:36])=[CH:30][N:29]=2)=[CH:24][CH:23]=1>CN(C)C=O.C(N(CC)CC)C.ClCCl>[C:1]([NH:4][CH:5]([C:10]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[N:33]=[C:32]([OH:34])[C:31]([C:35]([OH:37])=[O:36])=[CH:30][N:29]=2)=[CH:26][CH:27]=1)=[O:12])[CH2:6][CH:7]([CH3:8])[CH3:9])(=[O:3])[CH3:2]

参加物

7

反応物 3

HCID 1995acetyl-DL-leucineHCID 62365Isobutyl chloroformateHCID 178507442HCID 178507442、化合物

生成物 1

HCID 178474741HCID 178474741、化合物収率 71.4%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒2 回

反応条件

温度
-10 °C

実験手順

A solution of 13.0 g (75 mmol) of N-acetyl-DL-leucine, 10.5 ml (75 mmol) of triethylamine, and 150 ml of dichloromethane is stirred at -10° and 9.75 ml (75 mmol) of isobutyl chloroformate is added. The reaction mixture is stirred for 1/2 hour at -10° C. and a cold solution of 11.6 g (50 mmol) of 2-[4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid and 7.7 (55 mmol) of triethylamine in 200 ml of dimethylformamide is added. The mixture is stirred at 5° C. for 3 hrs and overnight at room temperature. The reaction mixture is evaporated and the residue treated with water. The pH is lowered to 2.5 with dilute hydrochloric acid and the solid filtered, washed with water, and dried to give 13.8 g of 2-[4-(N-acetyl-DL-leucylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid; mp 233°-235° C. dec.

後処理

  1. stirringThe mixture is stirred at 5° C. for 3 hrs and overnight at room temperature
  2. customThe reaction mixture is evaporated
  3. additionthe residue treated with water
  4. filtrationthe solid filtered
  5. washwashed with water
  6. customdried

出典と根拠

ORDレコード
ord-fceb47acaddf4b658971068ab3942754
出典データセット
uspto-grants-1982_01
特許番号
US04311699

関連ノート

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