HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

1,5-Diazabicyclo(5,4,0)undec-5-ene → 7beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4-carboxylic acid diphenylmethyl ester

HRID 26105
Notes
Print preview

Reaction equation

HRID 26105 reaction equation
[C:1]1([CH:7]([O:14][C:15](=[O:50])/[C:16](/[N:21]2[CH:24]([S:25]S(C3C=CC([N+]([O-])=O)=CC=3)(=O)=O)[CH:23]([NH:38][C:39](=[O:48])[CH2:40][O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:22]2=[O:49])=[C:17](\[O:19][CH3:20])/[CH3:18])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)/C=C\C.N12CCCCC1C=NCCC2>O1CCCC1.C1C=CC=CC=1>[C:8]1([CH:7]([O:14][C:15]([CH:16]2[N:21]3[C:22](=[O:49])[C@@H:23]([NH:38][C:39](=[O:48])[CH2:40][O:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[C@H:24]3[S:25][CH:18]=[C:17]2[O:19][CH3:20])=[O:50])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 643792Isocrotonic acidHCID 705571912-[4-(p-Nitrobenzenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid diphenylmethyl ester

Product 1

HCID 705584137beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4-carboxylic acid diphenylmethyl ester

Reagents, catalysts & solvents 2

HCID 241
Benzene
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 367 mg (0.5 mM) of a mixture consisting of 2-[4-(p-nitrobenzenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid diphenylmethyl ester and the corresponding isocrotonic acid dihenylmethyl ester, and 152 mg (1.0 mM) of 1,5-diazabicyclo[5.4.0]undec- 5-ene in 10 ml of dry tetrahydrofurane is stirred for 40 minutes at room temperature. The reaction mixture is diluted with benzene, washed successively with dilute hydrochloric acid, water and dilute aqueous sodium bicarbonate solution, dried over sodium sulphate and freed from the solvent in vacuo. The residue is chromatographed on acid-washed silica gel, using toluene/ethyl acetate, 7:1, as the running agent, whereby pure 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4-carboxylic acid diphenylmethyl ester is obtained. Subsequent elution with toluene/ethyl acetate, 2:1, results in the isolation of a mixture which in addition to 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4-carboxylic acid diphenylmethyl ester also contains 7βphenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester.

Workup

  1. washwashed successively with dilute hydrochloric acid, water and dilute aqueous sodium bicarbonate solution
  2. dry with materialdried over sodium sulphate
  3. customThe residue is chromatographed
  4. washon acid-washed silica gel

Sources & evidence

ORD record
ord-04ad8d5045a645ef85caa4e25b79c364
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04147864

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes