Hydrochloric Acid → HCID 70436618, compound

HRID 1679695Notes

Reaction equation

HRID 1679695 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:30](=[O:31])[N:12]2[C:13]([C:17]([O:19]CC3C=CC([N+]([O-])=O)=CC=3)=[O:18])=[CH:14][CH2:15][S:16][C@H:11]12)=[O:8].CO.O1CCCC1.Cl>[Pd].O.C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:30](=[O:31])[N:12]2[C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH2:15][S:16][C@H:11]12)=[O:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 70617193HCID 70617193, compound

Product 1

HCID 70436618HCID 70436618, compoundYield 92.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a mixture of p-nitrobenzyl 7-(2-thienyl)acetamido-3-cephem-4-carboxylate (2.0 g), methanol (40 ml), and tetrahydrofuran (40 ml) one adds 10% hydrochloric acid (1.4 ml) and 5% palladium on carbon (1.9 g), shakes the mixture under hydrogen atmosphere (1 atm.) at room temperature for 2.5 hours, pours into water, extracts with methylene chloride, washes with water, dries, concentrates, and crystallizes from ether to give 7-(2-thienyl)acetamido-3-cephem-4-carboxylic acid (1.30 g).

Workup

  1. customat room temperature
  2. customfor 2.5 hours
  3. customcrystallizes from ether

Sources & evidence

ORD record
ord-4555acf51ada44adb698a8ba51dc8e7a
Source dataset
uspto-grants-1978_03
Patent number
US04081595

Reaction notes

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