HCID 11801229, compound → (6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1834223Notes

Reaction equation

HRID 1834223 reaction equation
[NH2:1][C@@H:2]1[C:26](=[O:27])[N:4]2[C:5]([C:10]([O:12]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:11])=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]12>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[NH2:1][C@@H:2]1[C:26](=[O:27])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]12

Participants

5

Reactant 1

HCID 11801229HCID 11801229, compound

Product 1

HCID 6998927(6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 34.1%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 6422Trifluoroacetic acidSolvent2×HCID 22728543Water ethylacetateSolvent

Procedure

1.59 g (4 mmols) of diphenylmethyl 7β-amino-3-chloro-3-cephem-4-carboxylate are dissolved in 5 ml of trifluoroacetic acid at 0° and the solution is stirred for 15 minutes. The clear, pale yellow solution is diluted with 20 ml of toluene and then freed from excess trifluoroacetic acid and toluene under reduced pressure. The residue is dissolved in about 20 ml of water/ethyl acetate (1:1), the organic phase is separated off and the acid aqueous phase is brought to a pH of 3.0 with 20% strength triethylamine in methanol. The pale yellow precipitate is filtered off, washed with ethyl acetate and diethyl ether and dried under a high vacuum. 320 mg of 7β-amino-3-chloro-3-cephem-4-carboxylic acid are isolated as a pale yellow amorphous powder; thin layer chromatogram: Rf = 0.08 (silica gel, n-butanol/acetic acid/water, 67:10:23).

Workup

  1. customthe organic phase is separated off
  2. filtrationThe pale yellow precipitate is filtered off
  3. washwashed with ethyl acetate and diethyl ether
  4. customdried under a high vacuum

Sources & evidence

ORD record
ord-46e81f63d4214be8ad0b28e25aca846f
Source dataset
uspto-grants-1978_01
Patent number
US04069324

Reaction notes

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