Sodium Hydroxide → Sodium 5-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)furan-2-carboxylate

HRID 408853Notes

Reaction equation

HRID 408853 reaction equation
C[O:2][C:3]([C:5]1[O:9][C:8]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+:25]>>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][N:11]([CH2:10][C:8]2[O:9][C:5]([C:3]([O-:4])=[O:2])=[CH:6][CH:7]=2)[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:21])[CH3:22].[Na+:25]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 58055786Tert-butyl 4-((5-(methoxycarbonyl)furan-2-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 66661312Sodium 5-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)furan-2-carboxylateYield 89.7%

Procedure

Tert-butyl 4-((5-(methoxycarbonyl)furan-2-yl)methyl)piperazine-1-carboxylate (4.99 g, 15.39 mmol) and sodium hydroxide (0.616 g, 15.39 mmol) were combined and stirred at reflux for 3 hours. The reaction was concentrated under reduced pressure to give the title compound (4.59 g). MS (ESI) m/z 311.4 [M+H]+

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2fea7eac6d124c27beacf5f3087a8193
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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