Hydrochloric Acid → HCID 131723792, compound

HRID 2250827Notes

Reaction equation

HRID 2250827 reaction equation
Cl.[NH2:2][OH:3].[NH2:4][CH:5]1[CH:8]2[S:9][CH2:10][C:11]3[CH:15](O)[O:14][C:13](=[O:17])[C:12]=3[N:7]2[C:6]1=[O:18].C(=O)([O-])O.[Na+]>O>[NH2:4][CH:5]1[C:6](=[O:18])[N:7]2[C:12]([C:13]([OH:14])=[O:17])=[C:11]([CH:15]=[N:2][OH:3])[CH2:10][S:9][C@H:8]12

Participants

6

Reactant 4

HCID 313Hydrochloric Acid3×HCID 787Hydroxylamine2×HCID 516892Sodium BicarbonateHCID 18623119HCID 18623119, compound

Product 1

HCID 131723792HCID 131723792, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.26 g of the hydrochloride of hydroxylamine in 7.5 ml of water is treated under stirring at 0° with 4.74 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 and stirred for ca. 8 hours at 0° under nitrogen. The pH of the reaction mixture is adjusted to 3.5 using solid sodium hydrogen carbonate. 7-Amino-3-[(hydroxy-imino)methyl]-3-cephem-4-carboxylic acid precipitates in form of colourless crystals, which are filtered off, washed with ca. 5 ml of cold water and 5 ml of acetone and dried. b) 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-[(hydroxy-imino)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. custom7-Amino-3-[(hydroxy-imino)methyl]-3-cephem-4-carboxylic acid precipitates in form of colourless crystals, which
  2. filtrationare filtered off
  3. washwashed with ca. 5 ml of cold water and 5 ml of acetone
  4. customdried
  5. additionb) 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
  6. additionis treated
  7. stirringunder stirring at 4° with 2.67 g of N,O-bis-(trimethylsilyl)acetamide
  8. customA clear solution is obtained within 10 minutes
  9. stirringThe reaction mixture is stirred for ca. 2 hours under nitrogen at 4°
  10. customthe solvent is evaporated off
  11. additionThe residue is treated with 10 ml of isopropylalkohol
  12. customprecooled to 1°
  13. custom7-Amino-3-[(hydroxy-imino)methyl]-3-cephem-4-carboxylic acid precipitates in form of almost colourless crystals which
  14. filtrationare filtered off
  15. washwashed with 5 ml of acetone
  16. customdried

Sources & evidence

ORD record
ord-7cd09b39743f4a309311c1a92888e068
Source dataset
uspto-grants-2008_01
Patent number
US07317101B2

Reaction notes

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