Citric Acid → 6-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

HRID 1514708노트

반응식

HRID 1514708 반응식
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:18])=[N:6][CH:5]=1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>CO>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 866462566-[3-(3,4-Difluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

생성물 1

HCID 667181646-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester수율 85.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

6-[3-(3,4-Difluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (3.50 g, 9.35 mmol) in methanol (125 mL) was treated with sodium borohydride (737 mg, 18.7 mmol) for 30 min at room temperature. Addition of aqueous citric acid solution (10%, 300 mL) and extraction with ethyl acetate afforded the title compound (3.0 g, 85%) as a white solid. MS: m/e=377.2 [M+H]+.

출처 및 근거

ORD 기록
ord-0e745df3fff447908124d2ea63d2fbb3
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222246B2

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