Acetone → HCID 88157256, compound

HRID 992705Notes

Reaction equation

HRID 992705 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:44]/[O:45]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:8]([NH:10][C@@H:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:27])=[C:15]([S:18][CH2:19][C:20]4[CH:25]=[CH:24][N:23]=[CH:22][N:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.Cl.C(OCC)(=O)C.CC(C)=O>C(O)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:44]/[OH:45])/[C:8]([NH:10][C@@H:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([OH:28])=[O:27])=[C:15]([S:18][CH2:19][C:20]4[CH:25]=[CH:24][N:23]=[CH:22][N:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 88157495HCID 88157495, compound

Product 1

HCID 88157256HCID 88157256, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of diphenylmethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetamido]-3-[(pyrimidin-4-yl)methylthio]-3-cephem-4-carboxylate (1.57 g, 1.74 m mol) in formic acid (6.28 ml) was added conc. HCl (0.435 ml, 5.22 m mol) at 5° C. The mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into a mixture of ethyl acetate (43 ml) and acetone (22 ml). The precipitates were collected by filtration, and dried in vacuo. The crude product was desalted with HP-20. The eluent was concentrated to give precipitates. The precipitates were collected by filtration and dried in vacuo to give 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-[(pyrimidin-4-yl)methylthio]-3-cephem-4-carboxylic acid (128 mg, 0.259 m mol).

Workup

  1. filtrationThe precipitates were collected by filtration
  2. customdried in vacuo
  3. concentrationThe eluent was concentrated
  4. customto give
  5. customprecipitates
  6. filtrationThe precipitates were collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-baf3a5eb22f0498493ae7093ef2d4417
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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