Hydrochloric Acid → HCID 178475884, compound

HRID 358268Notes

Reaction equation

HRID 358268 reaction equation
[Na].[O:2]=[C:3]([CH:25]([CH3:27])[CH3:26])[CH2:4][C:5]([NH:7][C@@H:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH2:13][S:14][C@H:9]12)=[O:6].[N:28]([O-])=[O:29].[Na+].Cl>C(OCC)(=O)C.O.C(O)(=O)C>[OH:29][N:28]=[C:4]([C:3](=[O:2])[CH:25]([CH3:27])[CH3:26])[C:5]([NH:7][C@@H:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 23668193Sodium NitriteHCID 131713662HCID 131713662, compound

Product 1

HCID 178475884HCID 178475884, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6.1 g. of sodium salt of 7β-(3-oxo-4-methylvaleramido)-3-acetoxymethylceph-3-em-4-carboxylic acid in 60 ml. of glacial acetic acid, are dropped 2.1 g. of sodium nitrite dissolved in 20 ml. of water. After stirring for 2 hours at ambient temperature, there are added 200 ml. of ethyl acetate and 100 ml. of hydrochloric acid 0.1N. The phases are separated and the organic phase is washed with 50 ml. of water, made anhydrous, decolourised over charcoal and concentrated to small volume. The precipitated solid is filtered off to give 1.4 g of 7β-(2-hydroxyimino-3-oxo-4-methylvaleramido)-3-acetoxymethylceph-3-em-4-carboxylic acid melting at 156° C. (with decomposition); [α]D =+76.9° C. (c=2 in tetrahydrofuran/water 1:1).

Workup

  1. additionthere are added 200 ml
  2. customThe phases are separated
  3. washthe organic phase is washed with 50 ml
  4. concentrationconcentrated to small volume
  5. filtrationThe precipitated solid is filtered off

Sources & evidence

ORD record
ord-afd39e50e71b44f9b2022b85039f046b
Source dataset
uspto-grants-1984_08
Patent number
US04465831

Reaction notes

Loading…