Potassium Bromide → Clavulanic Acid

HRID 370440

반응식

HRID 370440 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)(O)[O-].[Na+].[K+].[Br-]>C(O)C.O.[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

7

반응물 3

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 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 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

Benzyl clavulanate (840 mgs) in ethanol (30 ml) and water (5 ml) was hydrogenated over 10% Pd/C (267 mgs) and sodium bicarbonate (244 mgs) for 25 minutes at room temperature and atmospheric pressure. The catalyst was filtered, washed with water and ethanol and the combined filtrates were evaporated in vacuo. The product crystallised from a water-acetone mixture as microneedles (565 mgs). Recrystallisation from water-acetone gave needles which, after drying over P2O5 in vacuo for 24 hours gave the following analysis: C 41.01, 40.86; H 3.77, 3.64; N 5.68, 5.51; i.r.(KBr disc) 1785, 1700, 1620 cm-1 ; Nmr (D2O) 3.06 (d,1,J=18.5 Hz), 3.57 (dd,1,J1 =18.5 Hz, J2 =2.5 Hz), 4.15 (d,2,J=8 Hz), 5.3 (HOD), 4.9(m), 5.71 (d,1,J=2.5 Hz).

후처리

  1. filtrationThe catalyst was filtered
  2. washwashed with water and ethanol
  3. customthe combined filtrates were evaporated in vacuo
  4. customThe product crystallised from a water-acetone mixture as microneedles (565 mgs)
  5. customRecrystallisation from water-acetone
  6. customgave needles which
  7. dry with materialafter drying over P2O5 in vacuo for 24 hours
  8. customgave the following analysis

출처 및 근거

ORD 기록
ord-245d07d2c781440a81b6e5d8c61452dc
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04526783

연결된 노트

불러오는 중…