Triethylamine → HCID 178502852, compound

HRID 2198558Notes

Reaction equation

HRID 2198558 reaction equation
[CH:1]1[C:6]([C@@H:7]([NH2:30])[C:8]([NH:10][C@@H:11]2[C:14](=[O:15])[N:13]3[C:16]([C:27]([OH:29])=[O:28])=[C:17]([CH2:20][S:21][C:22]4[N:26]=[N:25][NH:24][CH:23]=4)[CH2:18][S:19][C@H:12]23)=[O:9])=[CH:5][CH:4]=[C:3]([OH:31])[CH:2]=1.C(N(CC)CC)C>CO>[CH:5]1[C:6]([C@@H:7]([NH2:30])[C:8]([NH:10][C@@H:11]2[C:14](=[O:15])[N:13]3[C:16]([C:27]([OH:29])=[O:28])=[C:17]([CH2:20][S:21][C:22]4[N:26]=[N:25][NH:24][CH:23]=4)[CH2:18][S:19][C@H:12]23)=[O:9])=[CH:1][CH:2]=[C:3]([OH:31])[CH:4]=1.[CH3:8][O-:9]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 178511839HCID 178511839, compound

Product 1

HCID 178502852HCID 178502852, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

The combined extracts (upper layer + extracted layer) were combined and by adding cold methanol, the total volume was brought to 200 ml. This methanolic solution containing cefatrizine was added slowly to methanol, kept at a constant pH 5.1 by automatic addition of 10% triethylamine in methanol. The mixture was further stirred for one hour and then kept overnight at about -15° C. The crystalline precipitate was filtered, washed with 95% methanol and 99% methanol, respectively and dried in vacuo to constant weight. The yield was 8.408 g. of 7-[D-α-amino-p-hydroxyphenylacetamido]-3-[(1H)-1,2,3-triazol-5-yl-thiomethyl]-3-cephem-4-carboxylic acid-methanolate. The PMR spectrum of the product indicated an exact 1:1 ratio between cefatrizine and methanol, while crude yield of cefatrizine methanolate was 63.83%.

Workup

  1. waitkept overnight at about -15° C
  2. filtrationThe crystalline precipitate was filtered
  3. washwashed with 95% methanol and 99% methanol
  4. customrespectively and dried in vacuo to constant weight

Sources & evidence

ORD record
ord-00982cd811dc44c989814ca9c3b8b08c
Source dataset
uspto-grants-1982_11
Patent number
US04358588

Reaction notes

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