N-Acetyl-DL-methionine → HCID 178503723, 화합물

HRID 1106114

반응식

HRID 1106114 반응식
[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]

참가 물질

7

반응물 4

HCID 6180N-Acetyl-DL-methionineHCID 31374DimethylacetamideHCID 62365Isobutyl chloroformateHCID 178507442HCID 178507442, 화합물

생성물 1

HCID 178503723HCID 178503723, 화합물수율 57.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-05d69929a85042e98f25dfbd14c9cd8c
출처 데이터셋
uspto-grants-1982_01
특허 번호
US04311699

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