Hydrochloric Acid → HCID 57218105, compound

HRID 2352691Notes

Reaction equation

HRID 2352691 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:22]1[N:23]=[C:24]([NH2:27])[S:25][CH:26]=1)[C:5]([NH:7][CH:8]1[C:20](=[O:21])[N:10]2[C:11]([C:17](O)=[O:18])=[C:12]([CH2:15][OH:16])[CH2:13][S:14][C@H:9]12)=[O:6].Cl>CC(C)=O.O>[CH3:1][O:2][N:3]=[C:4]([C:22]1[N:23]=[C:24]([NH2:27])[S:25][CH:26]=1)[C:5]([NH:7][CH:8]1[CH:9]2[S:14][CH2:13][C:12]3[CH2:15][O:16][C:17](=[O:18])[C:11]=3[N:10]2[C:20]1=[O:21])=[O:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 44307984HCID 44307984, compound

Product 1

HCID 57218105HCID 57218105, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 7-[2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-hydroxymethyl-3-cephem-4-carboxylic acid (syn isomer) (0.3 g) in a mixture of acetone (3 ml) and water (1.5 ml) was adjusted to pH 2 with 6N hydrochloric acid and stirred for 4 hours at ambient temperature. After the acetone was distilled off, to the residue was added water (1 ml). The mixture was adjusted to pH 7 with a saturated aqueous solution of sodium bicarbonate and ice-cooled for 1 hour. Precipitating crystals were collected by filtration, washed with water and dried to give 6-[2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-5a,6-dihydro-3H, 7H-azeto[2,1-b]furo[3,4-d][1,3]-thiazine-1,7(4H)-dione (syn isomer) (0.23 g), mp 210° to 215° C. (dec.).

Workup

  1. distillationAfter the acetone was distilled off, to the residue
  2. additionwas added water (1 ml)
  3. temperaturecooled for 1 hour
  4. customPrecipitating crystals
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-7ff2f1395ef248aba8dc2b29d658be3c
Source dataset
uspto-grants-1989_10
Patent number
US04877873

Reaction notes

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