Diphenylmethyl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate → 3-Acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

HRID 443552Notes

Reaction equation

HRID 443552 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([NH:30][C:31](=[O:60])[C:32]([C:35]3[N:36]=[C:37]([NH:40]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:38][CH:39]=3)=[N:33][OH:34])[C:28](=[O:61])[N:10]2[C:11]=1[C:12]([O:14]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O.C(OC(C)C)(C)C>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([NH:30][C:31](=[O:60])[C:32]([C:35]3[N:36]=[C:37]([NH2:40])[S:38][CH:39]=3)=[N:33][OH:34])[C:28](=[O:61])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 131712161Diphenylmethyl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate

Product 1

HCID 1317117353-Acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7914Diisopropyl EtherSolvent

Procedure

The product of Step C was dissolved in 15 ml of pure trifluoroacetic acid and the mixture stood for 15 minutes and was then diluted with 100 ml of isopropyl ether. The mixture was stirred for 5 minutes and was vacuum filtered and the filter was rinsed with isopropyl ether. The product was dried and then dissolved in 2 ml of ethanol containing 0.2 ml of pyridine. The mixture was vacuum filtered and the recovered product was rinsed twice with ethanol to obtain the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Workup

  1. filtrationfiltered
  2. washthe filter was rinsed with isopropyl ether
  3. customThe product was dried
  4. dissolutiondissolved in 2 ml of ethanol containing 0.2 ml of pyridine
  5. filtrationfiltered
  6. washthe recovered product was rinsed twice with ethanol

Sources & evidence

ORD record
ord-86945a00047e4a2ea0a4a8920bdc23f1
Source dataset
uspto-grants-1981_04
Patent number
US04260747

Reaction notes

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