4-Methylmorpholine → HCID 178475081, 화합물

HRID 1106120노트

반응식

HRID 1106120 반응식
[C:1]([NH:4][C@@H:5]([C:9]([OH:11])=O)[CH:6]([CH3:8])[CH3:7])(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[N:39]=[C:38]([OH:40])[C:37]([C:41]([OH:43])=[O:42])=[CH:36][N:35]=2)=[CH:30][CH:29]=1.C(N(CC)CC)C>CN(C)C(=O)C.ClCCl>[C:1]([NH:4][C@@H:5]([C:9]([NH:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]2[N:39]=[C:38]([OH:40])[C:37]([C:41]([OH:43])=[O:42])=[CH:36][N:35]=2)=[CH:32][CH:33]=1)=[O:11])[CH:6]([CH3:7])[CH3:8])(=[O:3])[CH3:2]

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 76475N-acetyl-D-valineHCID 178507442HCID 178507442, 화합물

생성물 1

HCID 178475081HCID 178475081, 화합물수율 49.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 31374Dimethylacetamide용매

실험 절차

A suspension of 11.41 g (71.7 mmol) of N-acetyl-D-valine and 150 ml of dichloromethane is stirred at room temperature and 7.9 ml (71.7 mmol) of N-methylmorpholine is added. The resulting solution is cooled to -10° C. and 9.3 ml (71.7 mmol) of isobutyl chloroformate is added. The reaction mixture is stirred at -15°±5° C. for 45 min and an ice cold solution of 11.09 g (48 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid, 7.4 ml (52.8 mmol) of triethylamine, and 200 ml of N,N-dimethylacetamide is added while keeping the temperature below -10° C. The mixture is stirred at 0°-5° C. for 2 hrs and overnight at room temperature. A small amount of solid is filtered and the filtrate is evaporated to dryness. Water is added to the residue and the resulting solid filtered, washed with water, ethyl acetate, and ether and dried to give 8.9 g of 2-[4-(N-acetyl-D-valylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid. A second crop, obtained from the aqueous filtrate, weighs 2.35 g. [α]D23 +4.50 (cl, pH 7).

후처리

  1. temperatureThe resulting solution is cooled to -10° C.
  2. stirringThe reaction mixture is stirred at -15°±5° C. for 45 min
  3. customthe temperature below -10° C
  4. stirringThe mixture is stirred at 0°-5° C. for 2 hrs and overnight at room temperature
  5. filtrationA small amount of solid is filtered
  6. customthe filtrate is evaporated to dryness
  7. additionWater is added to the residue
  8. filtrationthe resulting solid filtered
  9. washwashed with water, ethyl acetate, and ether
  10. customdried

출처 및 근거

ORD 기록
ord-e9b9f4b2eb5a45d9985549e91d7b8bdb
출처 데이터셋
uspto-grants-1982_01
특허 번호
US04311699

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