N-Acetyl-DL-methionine → HCID 178503723、化合物

HRID 1106114

反応式

HRID 1106114 の反応式
[C:1]([NH:4][CH:5]([C:10]([OH:12])=O)[CH2:6][CH2:7][S:8][CH3:9])(=[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.CC(N(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][CH2:7][S:8][CH3:9])(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 6180N-Acetyl-DL-methionineHCID 31374DimethylacetamideHCID 62365Isobutyl chloroformateHCID 178507442HCID 178507442、化合物

生成物 1

HCID 178503723HCID 178503723、化合物収率 57.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒2 回

実験手順

A suspension of 14.34 g (75 mmol) of N-acetyl-DL-methionine and 150 ml of dichloromethane is stirred at -15° and 10.5 ml (75 mmol) of triethylamine is added followed by 9.75 ml (75 mmol) of isobutyl chloroformate. After stirring for 20 minutes at -15° C., a solution of 11.6 g (50 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid in 200 ml of dimethylacetamide containing 7.7 ml (55 mmol) of triethylamine is added at -15° C. The mixture is stirred at 0° C. for 3 hrs and overnight at room temperature. The mixture is evaporated and the residue triturated with water. The aqueous suspension, after adjusting the pH to 2.5 with dilute HCl is filtered, washed with water, and dried to give 11.54 g of 2-[4-(N-acetyl-DL-methionylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid; mp 259° C. dec.

後処理

  1. stirringAfter stirring for 20 minutes at -15° C.
  2. stirringThe mixture is stirred at 0° C. for 3 hrs and overnight at room temperature
  3. customThe mixture is evaporated
  4. customthe residue triturated with water
  5. filtrationis filtered
  6. washwashed with water
  7. customdried

出典と根拠

ORDレコード
ord-05d69929a85042e98f25dfbd14c9cd8c
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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