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

反応式

[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]

参加物

反応物 3

HCID 90495Di-tert-butyl dicarbonate

HCID 995005-Methoxy-o-toluidine

HCID 10707784Tert-butyl N-[5-methoxy-2-(2-oxopropyl)phenyl]carbamate

生成物 1

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

実験手順

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.