4-Methyl-2-oxovaleric acid → 4,4-Dimethoxy-2-isobutylbutanoic acid

HRID 326273

반응식

HRID 326273 반응식
COC(OC)C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:45][O:46][CH:47]([O:50][CH3:51])[CH2:48]Br.[CH3:52][CH:53]([CH3:60])[CH2:54][C:55](=O)[C:56]([OH:58])=[O:57]>>[CH3:45][O:46][CH:47]([O:50][CH3:51])[CH2:48][CH:55]([CH2:54][CH:53]([CH3:60])[CH3:52])[C:56]([OH:58])=[O:57]

참가 물질

5

반응물 4

HCID 704-Methyl-2-oxovaleric acidHCID 11776TriphenylphosphineHCID 816722-Bromo-1,1-dimethoxyethaneHCID 570811621,1-Dimethoxy-2-(triphenylphosphoranylidene)ethane

생성물 1

HCID 543594864,4-Dimethoxy-2-isobutylbutanoic acid

실험 절차

Alternatively, for those compounds wherein n=1 and R1 is H, the compounds can be prepared by condensing the ylide 1,1-dimethoxy-2-(triphenylphosphoranylidene) ethane prepared from triphenylphosphine and 1,1-dimethoxy-2-bromoethane with 4-methyl-2-oxopentanoic acid. The product is then hydrogenated to obtain 4,4-dimethoxy-2-isobutylbutanoic acid which is coupled to the moiety R3NHCHR4COX to obtain 4,4-dimethoxy-2-isobutylbutanoyl--NR3CHR4COX. Treatment with aqueous acid yields the aldehyde 2-isobutyl-4-oxobutanoyl--NR3CHR4COX. The oxime is prepared by reaction with hydroxylamine and reduced to the corresponding N-substituted hydroxylamine. Acylation of both the hydroxaminol oxygen and nitrogen followed by hydrolysis of the O-acyl group provides the N-acyl reverse hydroxymates. (Summers, J.B., et al., J Med Chem (1988) 31:1960-1964.)

출처 및 근거

ORD 기록
ord-d12e82eadbdf4628b606f1573211d8b5
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05268384

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