Hydrochloric Acid → HCID 23000820, compound

HRID 2288026Notes

Reaction equation

HRID 2288026 reaction equation
[CH:1]1([C:4]([CH:6]([N:14]2[CH2:19][CH2:18][CH:17]([SH:20])/[C:16](=[CH:21]/[C:22]([O:24]CC)=[O:23])/[CH2:15]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])=[O:5])[CH2:3][CH2:2]1.[ClH:27]>C(O)(=O)C>[ClH:27].[CH:1]1([C:4]([CH:6]([N:14]2[CH2:19][CH2:18][CH:17]([SH:20])/[C:16](=[CH:21]/[C:22]([OH:24])=[O:23])/[CH2:15]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15462955HCID 15462955, compound

Product 1

HCID 23000820HCID 23000820, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a mixed solvent of 15 ml of acetic acid and 10 ml of concentrated hydrochloric acid, 0.44 g (1.1 mmol) of (E)-1-(α-cyclopropylcarbonyl-2-fluorobenzyl)-3-ethoxycarbonylmethylidene-4-mercaptopiperidine were dissolved and the resulting solution was allowed to stand for 12 days at room temperature in a dark place. The reaction mixture was concentrated to dryness, followed by crystallization from ethyl ether. The crystals collected by filtration were purified by chromatography on a silica gel column (eluting solvent: chloroform/methanol=30/1), whereby 0.12 g (yield 27%) of the title compound were obtained as light yellowish white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customfollowed by crystallization from ethyl ether
  3. filtrationThe crystals collected by filtration
  4. customwere purified by chromatography on a silica gel column (eluting solvent: chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-1de4e408488a4039880f85c697ace903
Source dataset
uspto-grants-2000_07
Patent number
US06087379

Reaction notes

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