acetyl-DL-leucine → HCID 178474741, 화합물

HRID 1106115

반응식

HRID 1106115 반응식
[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]

참가 물질

7

반응물 3

HCID 1995acetyl-DL-leucineHCID 62365Isobutyl chloroformateHCID 178507442HCID 178507442, 화합물

생성물 1

HCID 178474741HCID 178474741, 화합물수율 71.4%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매2회

반응 조건

온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fceb47acaddf4b658971068ab3942754
출처 데이터셋
uspto-grants-1982_01
특허 번호
US04311699

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