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Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 2-(3-(((tert-butoxy)carbonyl)amino)cyclobutylidene)acetate

HRID 1855200
Notes
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Reaction equation

HRID 1855200 reaction equation
O=[C:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:3]1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])C=CC=CC=1>C1(C)C=CC=CC=1>[C:9]([O:8][C:7]([NH:6][CH:4]1[CH2:5][C:2](=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:3]1)=[O:13])([CH3:12])([CH3:11])[CH3:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 23374584tert-Butyl 3-oxocyclobutylcarbamate

Product 1

HCID 86701055Ethyl 2-(3-(((tert-butoxy)carbonyl)amino)cyclobutylidene)acetateYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 3-oxocyclobutylcarbamate (1.0 g, 5.4 mmol) in toluene (10 mL) was added ethyl 2-(triphenylphosphoranylidene)acetate (2.1 g, 5.9 mmol). The reaction mixture was heated at 100° C. for 2 hrs, and then concentrated. The residue was purified by silica gel column chromatography (10% EtOAc/petroleum ether) to afford ethyl 2-(3-(tert-butoxycarbonylamino)cyclobutylidene)acetate (1.2 g, 89%). ESI-MS (EI+, m/z): 256 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography (10% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-7aaba7c3a4dd4421b8d8458aef9a642d
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962843B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes