Acetone → HCID 131712381, compound

HRID 1577584Notes

Reaction equation

HRID 1577584 reaction equation
CC(C)=O.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[NH:13][C:14]([CH2:16][O:17][N:18]=[C:19]([C:43]1[N:44]=[C:45]([NH:48]C=O)[S:46][CH:47]=1)[C:20]([NH:22][CH:23]1[C:41](=[O:42])[N:25]2[C:26]([C:38]([OH:40])=[O:39])=[C:27]([CH2:30][S:31][C:32]3[N:36]([CH3:37])[N:35]=[N:34][N:33]=3)[CH2:28][S:29][C@H:24]12)=[O:21])=[O:15].Cl>CO>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[NH:13][C:14]([CH2:16][O:17][N:18]=[C:19]([C:43]1[N:44]=[C:45]([NH2:48])[S:46][CH:47]=1)[C:20]([NH:22][CH:23]1[C:41](=[O:42])[N:25]2[C:26]([C:38]([OH:40])=[O:39])=[C:27]([CH2:30][S:31][C:32]3[N:36]([CH3:37])[N:35]=[N:34][N:33]=3)[CH2:28][S:29][C@H:24]12)=[O:21])=[O:15]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 131712382HCID 131712382, compound

Product 1

HCID 131712381HCID 131712381, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of acetone (1 ml.), methanol (4 ml.) and 7-[2-{N-(2-hydroxy-5-chlorophenyl)carbamoylmethoxyimino}-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.55 g.) was added conc. hydrochloric acid (0.11 ml.) followed by stirring for 3 hours at room temperature. The reaction mixture was concentrated and then to the residue were added water (3 ml.) and an aqueous solution of sodium bicarbonate whereby the pH was adjusted to about 2. The resulting mixture was stirred at room temperature and the precipitates were collected by filtration, washed with water and then dried to give the title compound (0.40 g.), mp. 165° to 175° C. (dec.).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionto the residue were added water (3 ml.)
  3. stirringThe resulting mixture was stirred at room temperature
  4. filtrationthe precipitates were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-2d27ce45d2b54a989b92355ba78d1d00
Source dataset
uspto-grants-1981_09
Patent number
US04288435

Reaction notes

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