HCID 131710751, compound → HCID 88767746, compound

HRID 1707175Notes

Reaction equation

HRID 1707175 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:20]([NH:21][C:22](=[O:32])[C:23](=[N:30][OH:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:19](=[O:33])[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]([NH:21][C:22](=[O:32])[C:23](=[N:30][OH:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:19](=[O:33])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 131710751HCID 131710751, compound

Product 1

HCID 88767746HCID 88767746, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of t-butyl 3-acetoxymethyl-7β-[2-hydroxyimino-2-phenylacetamido]-ceph-3-em-4-carboxylate (syn-isomer) (1.45 g.) in trifluoroacetic acid (25 ml.) was allowed to stand at room temperature for 10 minutes. The trifluoroacetic acid was evaporated under reduced pressure, the residue dissolved in ether (50 ml.) and extracted with saturated aqueous sodium bicarbonate. The combined aqueous extracts were acidified (2 N hydrochloric acid) and extracted with ethyl acetate. The combined extracts were washed with water, dried and evaporated. The residue was redissolved in ethyl acetate (5 ml.) and added dropwise with stirring to petroleum (b.p. 40°-60° C.; 500 ml.). The precipitated solid was filtered and dried, giving 3-acetoxymethyl-7β-[2-hydroxyimino-2-phenylacetamido]-ceph-3-em-4-carboxylic acid (syn-isomer) (0.515 g; 42%), [α]D +56° (c 0.5, DMSO), λmax. (EtOH) 253 nm (ε 16,600), νmax. (Nujol) 3380 (NH and OH), 1778 (β-lactam), 1720 (CO2H and acetate), 1666 and 1540 cm.-1 (CONH) τ (DMSO-d6) values include 0.32 (doublet, J 9 Hz; NH) 2.15-2.7 (multiplet; aromatic protons), 7.8 (singlet; CH3CO).

Workup

  1. customThe trifluoroacetic acid was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in ether (50 ml.)
  3. extractionextracted with saturated aqueous sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with water
  6. customdried
  7. customevaporated
  8. dissolutionThe residue was redissolved in ethyl acetate (5 ml.)
  9. additionadded dropwise
  10. filtrationThe precipitated solid was filtered
  11. customdried

Sources & evidence

ORD record
ord-75b769e5104b4bcb805e43fa4732145b
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

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