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N-(5-methoxy-2-nitrophenyl)-N-t-butoxycarbonylcarbamic acid t-butyl ester → tert-Butyl (5-methoxy-2-nitrophenyl)carbamate

HRID 1061124
Notes
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Reaction equation

HRID 1061124 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24])C(OC(C)(C)C)=O)([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>C1(C)C=CC=CC=1.CO>[C:1]([O:5][C:6](=[O:26])[NH:7][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 9951148N-(5-methoxy-2-nitrophenyl)-N-t-butoxycarbonylcarbamic acid t-butyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 10199249tert-Butyl (5-methoxy-2-nitrophenyl)carbamateYield 75.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of N-(5-methoxy-2-nitrophenyl)-N-t-butoxycarbonylcarbamic acid t-butyl ester (10.6 g) in toluene (5 ml) and methanol (30 ml) was added 24% sodium methoxide in methanol (3.1 ml) and the mixture was stirred at 25° C. for 3 hours. At the end of this time the reaction mixture was cooled to 0° C. and the precipitated crystals were filtered to give the title compound (5.8 g, yield 75%).

Workup

  1. temperatureAt the end of this time the reaction mixture was cooled to 0° C.
  2. filtrationthe precipitated crystals were filtered

Sources & evidence

ORD record
ord-7d4c6fb7f6de48f491bd567fba25a4e4
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06525220B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes