3-(2-Hydroxy-ethylidene)-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester(benzyl calvunlanate) → Clavulanic Acid

HRID 371084

반응식

HRID 371084 반응식
[CH2:1]1[C:4](=[O:5])[N:3]2[C@@H:6]([C:12]([O:14]CC3C=CC=CC=3)=[O:13])/[C:7](/[O:11][C@H:2]12)=[CH:8]/[CH2:9][OH:10]>C(O)C.[Pd]>[CH2:1]1[C:4](=[O:5])[N:3]2[C@@H:6]([C:12]([OH:14])=[O:13])/[C:7](/[O:11][C@H:2]12)=[CH:8]/[CH2:9][OH:10]

참가 물질

4

반응물 1

HCID 99040553-(2-Hydroxy-ethylidene)-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester(benzyl calvunlanate)

생성물 1

HCID 5280980Clavulanic Acid

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

Benzyl clavulanate (100 mgs) in ethanol (5 ml) was hydrogenated over 10% Pd/C (30 mgs) for 45 minutes at ambient temperature and atmospheric pressure. The catalyst was filtered, washed with ethanol and the combined filtrates were evaporated in vacuo to give clavulanic acid as an unstable, viscous oil (58 mgs). N.m.r. (C5D5): 3.05(d,1,J=18 Hz), 3.60(dd,1,J1 =18 Hz), J2 =2.5 Hz), 4.75(d,2,J=7.5 Hz), 5.58(t,1,J=7.5 Hz),5.66 (S,1), 6.0δ(d,1,J=2.5 Hz).

후처리

  1. filtrationThe catalyst was filtered
  2. washwashed with ethanol
  3. customthe combined filtrates were evaporated in vacuo

출처 및 근거

ORD 기록
ord-7a9e5f71dc5d41738cbc9aabf09c21a3
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04529720

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