HCID 131713471, compound → HCID 131713470, compound

HRID 1904142Notes

Reaction equation

HRID 1904142 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:50])[C:19]([C:25]3[N:26]=[C:27]([NH:30]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:28][CH:29]=3)=[N:20][O:21][CH2:22][CH2:23][NH2:24])[C:15](=[O:51])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]>C(O)=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:50])[C:19]([C:25]3[N:26]=[C:27]([NH2:30])[S:28][CH:29]=3)=[N:20][O:21][CH2:22][CH2:23][NH2:24])[C:15](=[O:51])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 131713471HCID 131713471, compound

Product 1

HCID 131713470HCID 131713470, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1.054 g of the product of Step A and 5 ml of 70% aqueous formic acid was heated at 50° C. for 15 minutes and the mixture was vacuum filtered to remove triphenylcarbinol. The filtrate was evaporated to dryness under reduced pressure and the residue was taken up in water. The mixture was filtered and the filtrate was evaporated to dryness and the residue was taken up in ethanol. After efflorescence, the mixture was vacuum filtered to obtain 0.125 g of the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-(2-aminoethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. filtrationfiltered
  2. customto remove triphenylcarbinol
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. filtrationfiltered

Sources & evidence

ORD record
ord-168577334a7f421bb59a43a7e8394f21
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

Loading…