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

HRID 1061124Notes

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]

Participants

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

temperatureAt the end of this time the reaction mixture was cooled to 0° C.
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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