Diisopropyl Ether → HCID 137175473, compound

HRID 569407Notes

Reaction equation

HRID 569407 reaction equation
[CH:1]([NH:3][C:4]1[S:5][C:6]([C:9](=[N:40][O:41][CH3:42])[C:10]([NH:12][CH:13]2[C:38](=[O:39])[N:15]3[C:16]([C:22]([O:24]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:23])=[C:17]([CH:20]=[CH2:21])[CH2:18][S:19][C@H:14]23)=[O:11])=[CH:7][N:8]=1)=[O:2].C(OC(C)C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[CH:1]([NH:3][C:4]1[S:5][C:6]([C:9](=[N:40][O:41][CH3:42])[C:10]([NH:12][CH:13]2[C:38](=[O:39])[N:15]3[C:16]([C:22]([OH:24])=[O:23])=[C:17]([CH:20]=[CH2:21])[CH2:18][S:19][C@H:14]23)=[O:11])=[CH:7][N:8]=1)=[O:2]

Participants

5

Reactant 2

HCID 7914Diisopropyl EtherHCID 137175474HCID 137175474, compound

Product 1

HCID 137175473HCID 137175473, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of benzhydryl 7-[2-(2-formamidothiazol-5-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (2.7 g) in anisole (3.5 ml) and trifluoroacetic acid (10.8 ml) was stirred under ice-cooling for 15 minutes. The reaction mixture was poured into diisopropyl ether (140 ml), followed by stirring for 10 minutes. The precipitated solid was collected by filtration, washed with diisopropyl ether and then dried to give 7-[2-(2-formamidothiazol-5-yl)-2-methoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (2.0 g), mp 147° C. (dec.).

Workup

  1. temperaturecooling for 15 minutes
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with diisopropyl ether
  4. customdried

Sources & evidence

ORD record
ord-7315643d70ae4d65ba85ad59b24ce44b
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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