Methyl 4-(2-Fluoroethoxy)-2-hydroxybenzoate → Methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-(2-fluoroethoxy)benzoate

HRID 1787935Notes

Reaction equation

HRID 1787935 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([OH:15])[CH:6]=1.[C:16]([O:20][C:21]([NH:23][CH2:24][C:25]([CH3:29])([CH3:28])[CH2:26]O)=[O:22])([CH3:19])([CH3:18])[CH3:17]>>[C:16]([O:20][C:21]([NH:23][CH2:24][C:25]([CH3:29])([CH3:28])[CH2:26][O:15][C:7]1[CH:6]=[C:5]([O:4][CH2:3][CH2:2][F:1])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 10420774Methyl 4-(2-Fluoroethoxy)-2-hydroxybenzoateHCID 21263232tert-butyl N-(3-hydroxy-2,2-dimethylpropyl)carbamate

Product 1

HCID 86610266Methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-(2-fluoroethoxy)benzoateYield 72%

Procedure

Using a procedure similar to that of Example 26-B, methyl 4-(2-fluoroethoxy)-2-hydroxybenzoate (3.6 g, 17.8 mmol) is alkylated with 3-tert-butoxycarbonylamino-2,2-dimethylpropanol (3.62 g, 17.8 mmol) to afford methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-(2-fluoroethoxy)benzoate (5.12 g).

Sources & evidence

ORD record
ord-3391cfa1a6a840eebbbe1fab055a94af
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

Loading…