Ethylmorpholine → N-(3-Hydroxypyridine-2-carbonyl)glycine methyl ester

HRID 53830

반응식

HRID 53830 반응식
[OH:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.[CH3:12][O:13][C:14](=[O:17])[CH2:15][NH2:16].C(N1CCOCC1)C.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH3:12][O:13][C:14](=[O:17])[CH2:15][NH:16][C:8]([C:3]1[C:2]([OH:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10]

참가 물질

7

반응물 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 134013-Hydroxypicolinic AcidHCID 757711-HydroxybenzotriazoleHCID 122755Glycine methyl ester hydrochloride

생성물 1

HCID 15338188N-(3-Hydroxypyridine-2-carbonyl)glycine methyl ester수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3-Hydroxypyridine-2-carboxylic acid (6.96 g, 50 mmol), 6.28 g of glycine methyl ester hydrochloride, 6.4 ml of N-ethylmorpholine and 13.53 g of 1-hydroxy-1H-benzotriazole were suspended in 300 ml of anhydrous dichloromethane and a solution of 10.83 g of DCC (=N,N'-dicyclohexylcarbodiimide) in 50 ml of dichloromethane was added to this suspension at 0° C. After 12 hours, the mixture was filtered and the filtrate was washed with water and with a saturated aqueous solution of NaHCO3. Drying and concentrating yielded 7.33 g (70%) of N-(3-Hydroxypyridine-2-carbonyl)glycine methyl ester, m.p. 59°-61° C. (ethyl acetate/heptane), cf. example 1c) as well.

후처리

  1. filtrationthe mixture was filtered
  2. washthe filtrate was washed with water and with a saturated aqueous solution of NaHCO3
  3. customDrying
  4. concentrationconcentrating

출처 및 근거

ORD 기록
ord-999d4d543ba14997a65a392974d28294
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620995

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