Hydrochloric Acid → HCID 131710305, compound

HRID 328072Notes

Reaction equation

HRID 328072 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C@H:14]2[C:27](=[O:28])[N:16]3[C:17]([C:24]([OH:26])=[O:25])=[C:18]([CH:21]([CH3:23])[CH3:22])[CH2:19][S:20][C@H:15]23)=[O:12])=[CH:6][CH:5]=1)([O-])=O.Cl.[H][H]>CN(C)C=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C@H:14]2[C:27](=[O:28])[N:16]3[C:17]([C:24]([OH:26])=[O:25])=[C:18]([CH:21]([CH3:22])[CH3:23])[CH2:19][S:20][C@H:15]23)=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 131710303HCID 131710303, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131710305HCID 131710305, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The catalyst was added to a solution of 406 mg of DL cis 7-p-nitrophenylacetamido-3-isopropyl-3-cepheme-4-carboxylic acid in 3.8 ml of dimethylformamide and 1.12 ml of N hydrochloric acid and a current of hydrogen was passed therethrough until saturated. The mixture was filtered and the filter was washed with a 50--50 water-ethanol solution containing a few drops of hydrochloric acid. The filtrate was evaporated to dryness and the residue was taken up in 3 ml of water. Ammonium formate was added thereto to a pH of 4.5 and the mixture was stirred 5 minutes and vacuum filtered. The precipitate was empasted with water and dried to obtain DL cis 7-p-aminophenylacetamido-3-isopropyl-3-cepheme-4-carboxylic acid melting at 150° C with decomposition. The product occurred as ocre crystals slightly soluble in water, ethanol and chloroform and insoluble in ether.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter was washed with a 50--50 water-ethanol solution
  3. additioncontaining a few drops of hydrochloric acid
  4. customThe filtrate was evaporated to dryness
  5. additionAmmonium formate was added
  6. filtrationvacuum filtered
  7. customdried

Sources & evidence

ORD record
ord-f5d4b34ff2a24d5bb6bde6b947599eda
Source dataset
uspto-grants-1977_04
Patent number
US04016158

Reaction notes

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