Dacthal → HCID 12851074, compound

HRID 543541Notes

Reaction equation

HRID 543541 reaction equation
[SH:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.CC(O[CH2:15][C:16]1[CH2:25][S:24][C@@H:19]2[C@H:20]([NH2:23])[C:21](=[O:22])[N:18]2[C:17]=1[C:26]([OH:28])=[O:27])=O.COC(C1C(Cl)=C(Cl)C(C(OC)=O)=C(Cl)C=1Cl)=O>C(#N)C>[NH2:23][CH:20]1[C:21](=[O:22])[N:18]2[C:17]([C:26]([OH:28])=[O:27])=[C:16]([CH2:15][S:1][C:2]3[O:3][C:4]4[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=4[N:6]=3)[CH2:25][S:24][C@H:19]12

Participants

5

Reactant 3

HCID 2943DacthalHCID 4413287-Aminocephalosporanic acidHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 12851074HCID 12851074, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

A 1.66 g quantity of 2-mercaptobenzoxazole, 18 ml of acetonitrile and 2.72 g of 7-ACA were added to 14.9 g of DCPA with stirring under cooling at 10° C., and the reaction was allowed to proceed at 15° to 17° C. for 40 minutes. The reaction solution was cooled with ice and poured into 120 g of ice-water. The precipitate was recovered by filtration, washed with water (20 ml×4) and acetone successively, and dried thereby affording 3.35 g (92.3% of yield) of 7-amino-3-[(benzoxazol-2-yl)thiomethyl]-3-cephem-4-carboxylic acid.

Workup

  1. temperatureThe reaction solution was cooled with ice
  2. filtrationThe precipitate was recovered by filtration
  3. washwashed with water (20 ml×4) and acetone successively
  4. customdried

Sources & evidence

ORD record
ord-87d5628eeb4544ff977da6066bf08226
Source dataset
uspto-grants-1984_05
Patent number
US04446318

Reaction notes

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