Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylate → HCID 88485747, compound

HRID 2254047Notes

Reaction equation

HRID 2254047 reaction equation
[NH2:1][CH:2]1[C:27](=[O:28])[N:4]2[C:5]([C:11]([O:13][CH:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])=[C:6]([CH2:9][Cl:10])[CH2:7][S:8][C@H:3]12.[NH2:29][C:30]1[S:31][CH:32]=[C:33](/[C:35](=[N:48]/[O:49][CH:50]([C:59]([O:61][CH:62]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[O:60])[C:51]2[CH:56]=[CH:55][C:54]([OH:57])=[C:53]([OH:58])[CH:52]=2)/[C:36](ON2C3C=CC=CC=3N=N2)=[O:37])[N:34]=1>C1COCC1.C(OCC)(=O)C>[NH2:29][C:30]1[S:31][CH:32]=[C:33](/[C:35](=[N:48]/[O:49][CH:50]([C:59]([O:61][CH:62]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)=[O:60])[C:51]2[CH:56]=[CH:55][C:54]([OH:57])=[C:53]([OH:58])[CH:52]=2)/[C:36]([NH:1][CH:2]2[C:27](=[O:28])[N:4]3[C:5]([C:11]([O:13][CH:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[O:12])=[C:6]([CH2:9][Cl:10])[CH2:7][S:8][C@H:3]23)=[O:37])[N:34]=1

Participants

5

Reactant 2

HCID 13239626Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylateHCID 88485782HCID 88485782, compound

Product 1

HCID 88485747HCID 88485747, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diphenylmethyl 7-amino-3-chloromethyl3-cephem-4-carboxylate (VIa) (685 mg, 1.65 mmol) in THF (8.3 ml) was added benzotriazol-1-yl 2-(2-aminothiazol-4-yl)2-(Z)-(diphenylmethyloxycarbonyl-(3,4-dihydroxyphenyl) methyl]oxyiminoacetate (IIIa) (955 mg, 1.50 mmol) and the mixture was stirred for 5 hr at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water dried over MgSO4 and concentrated under reduced pressure. The crude product was chromatographed on a column of silica gel to afford 566 mg (41% yield) of the title compound.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-5a943252a29d4ede89f6bf3919cc1798
Source dataset
uspto-grants-1993_08
Patent number
US05234920

Reaction notes

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