HCID 14052374, compound → HCID 14052378, compound

HRID 255910Notes

Reaction equation

HRID 255910 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@@H:20]([O:21][CH3:22])[C:19](=[O:23])[N:10]2[C:11]=1[C:12]([O:14]C(C)(C)C)=[O:13])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@@H:20]([O:21][CH3:22])[C:19](=[O:23])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 14052374HCID 14052374, compound

Product 1

HCID 14052378HCID 14052378, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

t-Butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate (9.3 g) was dissolved in precooled trifluoroacetic acid (TFA) (100 ml) and stirred at 0° C. for 1 hour. The volatiles were removed first in vacuo, then under a stream of nitrogen. The residue was taken up in methylene chloride and washed with water and brine, dried over sodium sulfate and evaporated to give 6.5 g of 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylic acid.

Workup

  1. customThe volatiles were removed first in vacuo
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-5bc3b6947996495591c15a714b6bc732
Source dataset
uspto-grants-1987_10
Patent number
US04699904

Reaction notes

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