Hydrochloric Acid → HCID 14489186, compound

HRID 1376846Notes

Reaction equation

HRID 1376846 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]1[C:16](=[O:17])[N:15]2[CH:10]1[CH2:11][S:12][C:13]([S:31][CH3:32])=[C:14]2[C:18]([O:20]CC1C=CC([N+]([O-])=O)=CC=1)=[O:19])=[O:7])([CH3:4])[CH3:3].O1CCCC1.[H][H].Cl>CO>[CH3:4][C:2]([O:5][C:6]([NH:8][CH:9]1[C:16](=[O:17])[N:15]2[CH:10]1[CH2:11][S:12][C:13]([S:31][CH3:32])=[C:14]2[C:18]([OH:20])=[O:19])=[O:7])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14489182HCID 14489182, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14489186HCID 14489186, compoundYield 124.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.45 g of (6RS) (7RS) (4-nitrophenyl)-methyl 7-[(1,1-dimethylethyl)-oxycarbonyl-amino]-3-methylthio-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en 2-carboxylate, 30 ml of tetrahydrofuran, 30 ml of methanol and 1.45 g of 10% palladized carbon were hydrogenated under a pressure of 2 atmospheres of hydrogen, while being vigorously stirred. After one hour, the pressure was taken up to ambient, and under an inert atmosphere, 4 ml of N hydrochloric acid were added. After separation, the solvent was expelled under reduced pressure at 35° C. and the residue was taken up in 100 ml of distilled water. The mixture was extracted with methylene chloride and the organic phase was dried, and evaporated to dryness under reduced pressure to obtain 1.3 g of (6RS) (7RS) 7-[(1,1-dimethylethyl)-oxycarbonyl-amino]-3-methylthio-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylic acid.

Workup

  1. additionwere added
  2. customAfter separation
  3. customwas expelled under reduced pressure at 35° C.
  4. extractionThe mixture was extracted with methylene chloride
  5. customthe organic phase was dried
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e44116e5f54744b4bb819b33c0ef0488
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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