HCID 178494274, compound → HCID 178494275, compound

HRID 441950Notes

Reaction equation

HRID 441950 reaction equation
[CH3:1][O:2][C:3]1([NH:36][C:37](=[O:46])[CH:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[OH:39])[C:34](=[O:35])[N:5]2[C:6]([C:18]([O:20]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:19])=[C:7]([CH:10]([S:12][C:13]3[NH:17][N:16]=[N:15][N:14]=3)[CH3:11])[CH2:8][S:9][C@H:4]12>C1COCC1.C(O)=O>[CH3:1][O:2][C:3]1([NH:36][C:37](=[O:46])[CH:38]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[OH:39])[C:34](=[O:35])[N:5]2[C:6]([C:18]([OH:20])=[O:19])=[C:7]([CH:10]([S:12][C:13]3[NH:14][N:15]=[N:16][N:17]=3)[CH3:11])[CH2:8][S:9][C@H:4]12

Participants

4

Reactant 1

HCID 178494274HCID 178494274, compound

Product 1

HCID 178494275HCID 178494275, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester, 100 mg. was dissolved in 1 ml of a 50:50 mixture of THF and 97% formic acid at 0° C. The mixture was allowed to warm to room temperature and was then evaporated to dryness. Ethyl acetate was added to dissolve the residue and the solution was extracted twice with a saturated solution of sodium bicarbonate. The bicarbonate extracts were combined and were then acidified with dilute hydrochloric acid to pH 2.5. The product was extracted from the acidified bicarbonate extracts with ethyl acetate. The ethyl acetate was dried and evaporated to yield 53 mg of product, 7-methoxy-7-mandelamido-3-(1-methyltetrazole-5-ylthiomethyl)-3-cephem-4-carboxylic acid having the following NMR spectrum (60 megacycles run in acetone d6)

Workup

  1. customwas then evaporated to dryness
  2. additionEthyl acetate was added
  3. dissolutionto dissolve the residue
  4. extractionthe solution was extracted twice with a saturated solution of sodium bicarbonate
  5. extractionThe product was extracted from the acidified bicarbonate
  6. dry with materialThe ethyl acetate was dried
  7. customevaporated

Sources & evidence

ORD record
ord-5783b895a20d4207bff763bdaf28f294
Source dataset
uspto-grants-1977_08
Patent number
US04044000

Reaction notes

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