Hydrochloric Acid → HCID 131712062, compound

HRID 2285633Notes

Reaction equation

HRID 2285633 reaction equation
[Na+:1].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([NH:10][C@@H:11]1[C:23](=[O:24])[N:13]2[C:14]([C:20]([O-:22])=[O:21])=[C:15]([CH2:18][OH:19])[CH2:16][S:17][C@H:12]12)=[O:9].C(N(CC)CC)C.[CH2:32]=[C:33]1[O:37][C:35](=[O:36])[CH2:34]1.Cl>CN(C)C=O>[Na+:1].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([NH:10][C@@H:11]1[C:23](=[O:24])[N:13]2[C:14]([C:20]([O-:22])=[O:21])=[C:15]([CH2:18][O:19][C:35](=[O:36])[CH2:34][C:33](=[O:37])[CH3:32])[CH2:16][S:17][C@H:12]12)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12661DiketeneHCID 23695995Desacetylcephalothin sodium

Product 1

HCID 131712062HCID 131712062, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (20 ml) was dissolved 7β-(2-thienylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylic acid sodium salt (3.86 g) and, at -5° C., triethylamine (1.40 ml) and diketene (1.50 ml) were added. The reaction was carried out at -5°-0° C. for 1 hour, after which time the reaction mixture was poured in ice-water (200 ml). The mixture was adjusted to pH 2.0 with 4 N-hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was rinsed with water, diluted with water, brought to pH 7.0 with 5% aqueous sodium hydrogen carbonate solution and separated. The water layer was taken, concentrated and subjected to column-chromatography on Amberlite XAD-2, elution being carried out with water-methanol. The eluate was lyophilized. The above procedure provided 7β-(2-thienylacetamido)-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid sodium salt (4.48 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was rinsed with water
  3. additiondiluted with water
  4. customseparated
  5. concentrationconcentrated
  6. washsubjected to column-chromatography on Amberlite XAD-2, elution

Sources & evidence

ORD record
ord-0404217262de4f699feb874e8892b6af
Source dataset
uspto-grants-1982_04
Patent number
US04323676

Reaction notes

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