Di-tert-butyl dicarbonate → tert-Butyl (5-methoxy-2-methylphenyl)carbamate

HRID 1069579Notes

Reaction equation

HRID 1069579 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH2:17]C(=O)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(C)=C(C=1)N.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 995005-Methoxy-o-toluidineHCID 10707784Tert-butyl N-[5-methoxy-2-(2-oxopropyl)phenyl]carbamate

Product 1

HCID 10609920tert-Butyl (5-methoxy-2-methylphenyl)carbamateYield 80%

Procedure

1-[2-(tert-Butoxycarbonylamino)-4-methoxyphenyl]-2-propanone. 12 g (87 mmol) of 5-methoxy-2-methylaniline was treated by the method in Example 1, Part A, with 19 g (87 mmol) of di-tert-butyl dicarbonate to give on concentrating a reaction mixture containing 16.4 g (80% yield) of N-tert-butoxycarbonyl-5-methoxy-2-methylaniline. This material (69 mmol) was reacted with 106 mL of 1.3M sec-butyl lithium in cyclohexane and then 7.1 g (69 mmol) of N-methoxy-N-methylacetamide (as described in Example 9, Part B) to give after chromatography on silica, eluting with 33% EtOAc/hexane, 13.8 g (72% yield) of 1-[2-(tert-butoxycarbonylamino)-4-methoxyphenyl]-2-propanone.

Workup

  1. customto give
  2. concentrationon concentrating a reaction mixture

Sources & evidence

ORD record
ord-9cda172e70f84312af55310840a7fbaf
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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