Hydrochloric Acid → HCID 15725085, compound

HRID 867421Notes

Reaction equation

HRID 867421 reaction equation
[C:1]([NH:4][C@@H:5]([C:10]([OH:12])=[O:11])[C:6]([SH:9])([CH3:8])[CH3:7])(=[O:3])[CH3:2].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.Cl>CCOCC>[C:1]([N:4]1[C@@H:5]([C:10]([OH:12])=[O:11])[C:6]([CH3:7])([CH3:8])[S:9][C@@H:18]1[C:17]1[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 65532N-acetyl-D-penicillamineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 15725085HCID 15725085, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution containing 5.74 g (30 mmoles) of N-acetyl-D-penicillamine and 3.2 ml of 4-fluorobenzaldehyde in 20 ml of ether saturated with gaseous hydrogen chloride is stirred. After 5 to 6 minutes an oil separates which becomes crystalline after 30 minutes on rubbing. The precipitate is filtered out and washed with ether to give the title acid in a yield of 7.81 g (87.1%) which can be recrystallized from ethyl acetate, m.p. 144°-146° C., [α]D20 =+206.9°.

Workup

  1. filtrationThe precipitate is filtered out
  2. washwashed with ether

Sources & evidence

ORD record
ord-1ecd5353655e40f0beedee60d8410166
Source dataset
uspto-grants-1988_10
Patent number
US04775675

Reaction notes

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