Hydrochloric Acid → HCID 86737046, compound

HRID 1706515Notes

Reaction equation

HRID 1706515 reaction equation
[C:1]([CH:4]([N:14]1[CH2:17][CH:16]([NH:18][C:19](=[O:43])[C:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH:32]([C:40]([OH:42])=[O:41])[NH:33]C(=O)C(F)(F)F)=[CH:25][CH:24]=2)=[N:21][OH:22])[C:15]1=[O:44])[C:5]1[CH:10]=[C:9]([Br:11])[C:8]([OH:12])=[C:7]([Br:13])[CH:6]=1)([OH:3])=[O:2].[OH-].[Na+].Cl>O>[C:1]([CH:4]([N:14]1[CH2:17][CH:16]([NH:18][C:19](=[O:43])[C:20]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][CH:32]([NH2:33])[C:40]([OH:42])=[O:41])=[CH:27][CH:28]=2)=[N:21][OH:22])[C:15]1=[O:44])[C:5]1[CH:10]=[C:9]([Br:11])[C:8]([OH:12])=[C:7]([Br:13])[CH:6]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86737047HCID 86737047, compound

Product 1

HCID 86737046HCID 86737046, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(α-Carboxy-3,5-dibromo-4-hydroxybenzyl)-3-[2-[4-{3-carboxy-3-(2,2,2-trifluoroacetamido)propoxy}phenyl]-2-hydroxyiminoacetamido]-2-azetidinone (0.50 g.) was suspended in water (3 ml.), and 1N-sodium hydroxide aqueous solution (3 ml) was added to said suspension, and then the solution was stirred for 30 minutes. The reaction mixture was adjusted to pH 3 with 10% hydrochloric acid under ice-cooling. The precipitated crystals were collected by filtration, and the crystals were dissolved in a small amount of a sodium bicarbonate aqueous solution, and then the solution was treated with activated carbon. After the treatment, the solution was adjusted to pH 4 with 10% hydrochloric acid under ice-cooling, and the precipitate was collected by filtration to give 1-(α-carboxy-3,5-dibromo-4-hydroxybenzyl)-3-[2-{4-(3-amino-3-carboxypropoxy)phenyl}-2-hydroxyiminoacetamido]-2-azetidinone (40 mg.). Furthermore, the same compound (60 mg.) was recovered from the mother liquor. Total yield was 100 mg. Mp 190° to 194° C. (dec.).

Workup

  1. temperaturecooling
  2. filtrationThe precipitated crystals were collected by filtration
  3. dissolutionthe crystals were dissolved in a small amount of a sodium bicarbonate aqueous solution
  4. additionthe solution was treated with activated carbon
  5. temperaturecooling
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-8a8eff38843945b48a46e181b3c0f47f
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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