tert-Butyl (4-formylphenyl)carbamate → HCID 86591895, compound

HRID 1883116Notes

Reaction equation

HRID 1883116 reaction equation
C[O-].[Na+].[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:8][CH:7]=1)=O.[CH3:20][O:21][C:22](=[O:27])[CH2:23][N:24]=[N+:25]=[N-:26]>CO>[N:24](/[C:23](=[CH:4]/[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19])=[CH:8][CH:7]=1)/[C:22]([O:21][CH3:20])=[O:27])=[N+:25]=[N-:26]

Participants

5

Reactant 3

HCID 2771821tert-Butyl (4-formylphenyl)carbamateHCID 4020482Methyl 2-azidoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 86591895HCID 86591895, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution 13.45 mmol of sodium methoxide in 6 mL absolute methanol at 0° C. was added a solution of 717 mg (3.24 mmol) of tert-butyl 4-formylphenylcarbamate and 1.49 g (12.96 mmol) methylazidoacetate dissolved in 6 mL absolute methanol dropwise over 5 minutes. The mixture was stirred at 0° C. for 6 h, then partitioned between ethyl acetate and acetic acid until neutral. The organic phase was dried over magnesium sulfate, concentrated and purified by column chromatography, eluting with 25% ethyl acetate/hexane to provide 551 mg of methyl (2E)-2-azido-3-{4-[(tert-butoxycarbonyl)amino]phenyl}prop-2-enoate as a yellow solid.

Workup

  1. custompartitioned between ethyl acetate and acetic acid until neutral
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. custompurified by column chromatography
  5. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ced6808ffe25494eb18efa5b7c0527a5
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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