Ethanol → HCID 178472820, compound

HRID 1596615Notes

Reaction equation

HRID 1596615 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:11][C@H:10]([NH:12][OH:13])[CH2:9]2)=[CH:4][CH:3]=1.[N:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:15]=[O:16].CCO>C1COCC1>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][NH:14][C:15]([N:12]([C@H:10]1[CH2:11][C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9]1)[OH:13])=[O:16])[CH3:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 76283Ethyl isocyanatoacetateHCID 178526348HCID 178526348, compound

Product 1

HCID 178472820HCID 178472820, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of cis-3-(4-fluorophenyl)cyclobutylhydroxylamine (0.9 g, 5 mmol) in THF (20 ml) was added ethyl isocyanatoacetate (0.71 g, 5.5 mmol). After stirring for 10 minutes, EtOH was added. Volatiles were removed in vacuo and the resulting residue was recrystallized from ethyl acetate/n-hexane to afford 1.10 g (71% yield) of the title compound as colorless needles, m.p. 130-132° C.

Workup

  1. customVolatiles were removed in vacuo
  2. customthe resulting residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-96df2a8cd4ec457fa0f76f32b75bb0d1
Source dataset
uspto-grants-2001_09
Patent number
US06291520B1

Reaction notes

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