Diethyl Ether → tert-butyl (1S,3S)-3-{[difluoro(4-methylphenyl)acetyl]amino}cyclopentylcarbamate

HRID 271391Notes

Reaction equation

HRID 271391 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3]1.[F:15][C:16]([F:29])([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[C:17](OCC)=[O:18].CCOCC.CCCCCC>CCO>[F:15][C:16]([F:29])([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[C:17]([NH:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:3]1)=[O:18]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 14888699Ethyl 2,2-difluoro-2-(p-tolyl)acetateHCID 45091937tert-Butyl N-((1S,3S)-3-aminocyclopentyl)carbamate

Product 1

HCID 59834916tert-butyl (1S,3S)-3-{[difluoro(4-methylphenyl)acetyl]amino}cyclopentylcarbamateYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl [(1S,3S)-3-aminocyclopentyl]carbamate (1.36 g, 6.8 mmol) and ethyl difluoro(4-methylphenyl)acetate (1.45 g, 6.8 mmol) in EtOH (5 mL) was stirred at reflux for 16 h. The solution was cooled to rt. whereupon it solidified. Et2O (6 mL) and hexane (3 mL) were added and the mixture was stirred for 3 h and the solids collected by filtration, rinsing with Et2O (2 mL), and dried to give the title compound (1.051 g) as a solid; MS=313.4 (M+1-isobutylene).

Workup

  1. temperatureat reflux for 16 h
  2. filtrationthe solids collected by filtration
  3. washrinsing with Et2O (2 mL)
  4. customdried

Sources & evidence

ORD record
ord-e8e34dd190884ddc986aaa8d68156ca6
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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