Penicillin V → 1-(3,3-Dimethyl-7-oxo-6([phenoxy acetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-oyloxy)-3-(z,z,z-octadeca-6,9,12-trienoyloxy)propane

HRID 28302

반응식

HRID 28302 반응식
[CH3:1][C:2]1([CH3:24])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:21]([OH:23])=[O:22].[C:25]([O:44][CH2:45][CH2:46][CH2:47]O)(=[O:43])[CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].C1(N=C=NC2CCCCC2)CCCCC1>CN(C1C=CN=CC=1)C.ClCCl.CCCCCC>[CH3:1][C:2]1([CH3:24])[S:6][CH:5]2[N:4]([C:8](=[O:9])[CH:7]2[NH:10][C:11](=[O:12])[CH2:13][O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:3]1[C:21]([O:23][CH2:47][CH2:46][CH2:45][O:44][C:25](=[O:43])[CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:22]

참가 물질

7

반응물 3

HCID 6869Penicillin VHCID 10868DicyclohexylcarbodiimideHCID 103371121-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

생성물 1

HCID 867589501-(3,3-Dimethyl-7-oxo-6([phenoxy acetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-oyloxy)-3-(z,z,z-octadeca-6,9,12-trienoyloxy)propane

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

A mixture of penicillin V (1 g, 2.9 mmol), 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane (860 mg, 2.6 mmol), 1,3-dicyclohexylcarbodiimide (620 mg, 3 mmol) and 4-(N,N-dimethylamino)pyridine (catalytic amount) in dichloromethane (30 ml) was stirred overnight at room temperature. The reaction mixture was diluted with hexane (50 ml), filtered and concentrated to dryness. The residue was washed with hexane (3×50 ml) to remove unreacted 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane. The semisolid residue was disolved in diethyl ether (150 ml), washed with water (100 ml) and dried. The ether solution was diluted with hexane (125 ml) and the solution filtered through a bed of silica (4 cm×4 cm). The filtrate was concentrated, yielding 1-(3,3-dimethyl-7-oxo-6([phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptan-2-oyloxy)-3-(z,z,z-octadeca-6,9,12-trienoyloxy)propane as a viscous colourless oil.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated to dryness
  3. washThe residue was washed with hexane (3×50 ml)
  4. customto remove unreacted 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane
  5. washwashed with water (100 ml)
  6. customdried
  7. additionThe ether solution was diluted with hexane (125 ml)
  8. filtrationthe solution filtered through a bed of silica (4 cm×4 cm)
  9. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-bbc36ccbaa8240af95e1fbea003c5245
출처 데이터셋
uspto-grants-2008_09
특허 번호
USRE040480E1

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