Hydrochloric Acid → HCID 131723792, compound

HRID 1860474Notes

Reaction equation

HRID 1860474 reaction equation
Cl.[NH2:2][CH:3]1[CH:6]2[S:7][CH2:8][C:9]3[CH:13](O)[O:12][C:11](=[O:15])[C:10]=3[N:5]2[C:4]1=[O:16].[NH2:17][OH:18]>ClCCl>[NH2:2][CH:3]1[C:4](=[O:16])[N:5]2[C:10]([C:11]([OH:12])=[O:15])=[C:9]([CH:13]=[N:17][OH:18])[CH2:8][S:7][C@H:6]12

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 787HydroxylamineHCID 18623119HCID 18623119, compound

Product 1

HCID 131723792HCID 131723792, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 0.79 g of the hydrochloride of 6-amino-1,4,5a,6-tetrahydro-3-hydroxy-1,7-dioxo-3H,7H-azeto[2,1-b]furo[3,4-d][1,3]thiazin in 10 ml of dichloromethane is treated under stirring at 4° with 2.67 g of N,O-bis-(trimethylsilyl)acetamide. A clear solution is obtained within 10 minutes. 0.21 g of the hydrochloride of hydroxylamine are added. The reaction mixture is stirred for ca. 2 hours under nitrogen at 4° and the solvent is evaporated off. The residue is treated with 10 ml of isopropylalkohol, precooled to 1°. 7-Amino-3-[(hydroxyimino)methyl]-3-cephem-4-carboxylic acid precipitates in form of almost colourless crystals which are filtered off, washed with 5 ml of acetone and dried.

Workup

  1. additionis treated
  2. customA clear solution is obtained within 10 minutes
  3. customthe solvent is evaporated off
  4. additionThe residue is treated with 10 ml of isopropylalkohol
  5. customprecooled to 1°
  6. custom7-Amino-3-[(hydroxyimino)methyl]-3-cephem-4-carboxylic acid precipitates in form of almost colourless crystals which
  7. filtrationare filtered off
  8. washwashed with 5 ml of acetone
  9. customdried

Sources & evidence

ORD record
ord-14b3a293cc7b4e31845219b9209a6323
Source dataset
uspto-grants-2003_03
Patent number
US06531465B1

Reaction notes

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