Hydrochloric Acid → 3-Methyl-7beta-phenoxyacetamidoceph-3-em-4-carboxylic acid

HRID 1872313Notes

Reaction equation

HRID 1872313 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[C@H:16]([NH:17][C:18](=[O:27])[CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15](=[O:28])[N:6]2[C:7]=1[C:8]([O:10]C(C)(C)C)=[O:9].Cl>ClCCl.O.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[C@H:16]([NH:17][C:18](=[O:27])[CH2:19][O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:15](=[O:28])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 15379240t-Butyl 3-Methyl-7beta-phenoxyacetamidoceph-3-em-4-carboxylate

Product 1

HCID 111318273-Methyl-7beta-phenoxyacetamidoceph-3-em-4-carboxylic acidYield 86.1%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of tert-butyl (6R,7R)-3-methyl-7-phenoxyacetamido-ceph-3-em-4-carboxylate (0.41 g, 1.0 mmol) in dichloromethane (25 ml) was cooled to 0° C. Titanium tetrachloride (0.38 ml, 3.5 mmol) was added in 1 min. A yellow precipitate was formed which was stirred for 2 h at 0° C. To the suspension was added a chilled 1 M solution of hydrochloric acid in water (40 ml). The organic phase was separated, washed with water and brine, dried over magnesium sulphate, and evaporated to give 0.30 g of (6R,7R)-3-methyl-7-phenoxyacetamidoceph-3-em-4-carboxylic acid (purity 63%, yield 54.3%).

Workup

  1. customA yellow precipitate was formed which
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-59658c48db5641689af98a1bdd898c67
Source dataset
uspto-grants-2000_08
Patent number
US06107481

Reaction notes

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