Formic Acid → Triphenylcarbinol
Reaction equation
C(OCC1CS[C@@H]2C(NC(=O)C(C3N=C(N[C:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)SC=3)=NOC(C)C)C(=O)N2C=1C(O)=O)(=O)C.C(O)=[O:53]>O>[C:32]1([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[OH:53])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 4.91 g of raw product of Example 12 in 30 ml of 50% aqueous formic acid was stirred in a water bath at 60° C. and was then diluted with water and vacuum filtered. The filter was rinsed with water and the product was dried to obtain 1.39 g of triphenylcarbinol. The filtrate was evaporated to dryness and the residue was taken up in water and effloresced. The mixture was vacuum filtered and therecovered product was rinsed with water and dried to obtain 800 mg of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-(1-methylethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid. 972 mg of the product were dissolved in 4 ml of methanol and the solution was diluted with 20 ml of ether and vacuum filtered. The product was rinsed and dried to obtain 404 mg of the said acid for analysis in the syn configuration and melting at ≃200° C.
Workup
- filtrationfiltered
- washThe filter was rinsed with water
- customthe product was dried
Sources & evidence
- ORD record
- ord-baab594b939e4ff2a9b17d11b06a4fb4
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04843164
Reaction notes
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