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Cyclobutanone → [4-(1-Cyanocyclobutylamino)phenyl]acetic acid

HRID 1927354
Notes
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Reaction equation

HRID 1927354 reaction equation
C[Si]([C:5]#[N:6])(C)C.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.[C:18]1(=O)[CH2:21][CH2:20][CH2:19]1>O1CCOCC1>[C:5]([C:18]1([NH:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:12][CH:13]=2)[CH2:21][CH2:20][CH2:19]1)#[N:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 145334-Aminophenylacetic acidHCID 82115Trimethylsilyl cyanide

Product 1

HCID 67132001[4-(1-Cyanocyclobutylamino)phenyl]acetic acidYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Trimethylsilyl cyanide (0.69 g, 7 mmol) was added dropwise to a mixture of 4-aminophenylacetic acid (0.755 g, 5 mmol) and cyclobutanone (0.49 g, 7 mmol) in dioxane (20 ml). The mixture was stirred for 8 hours at 80° C. The mixture was concentrated and chromatographed (dichloromethane:acetone, 60:40) to yield [4-(1-cyanocyclobutylamino)phenyl]acetic acid (46a) (1.138 g, 4.95 mmol, 99%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed (dichloromethane:acetone, 60:40)

Sources & evidence

ORD record
ord-c2bd981477794df5aced6f2af40fa1f8
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08183274B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes