tert-butyl N-(3-hydroxy-2,2-dimethylpropyl)carbamate → Methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-(2-methoxyethoxy)benzoate

HRID 1787941Notes

Reaction equation

HRID 1787941 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:17]([O:21][C:22]([NH:24][CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27]O)=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[C:17]([O:21][C:22]([NH:24][CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][O:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 21263232tert-butyl N-(3-hydroxy-2,2-dimethylpropyl)carbamateHCID 23024267HCID 23024267, compound

Product 1

HCID 68832578Methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-(2-methoxyethoxy)benzoateYield 85.6%

Procedure

Using a procedure similar to that of Example 26-B, methyl 2-hydroxy-4-(2-methoxyethoxy)benzoate (3.2 g, 14.14 mmol) is alkylated with 3-tert-butoxycarbonylamino-2,2-dimethylpropanol (2.88 g, 14.14 mmol) to afford methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-(2-methoxyethoxy)benzoate (4.982 g) after purification over silica gel, eluting with a gradient of 0-40% ethyl acetate in hexane.

Sources & evidence

ORD record
ord-c2dc5be7370c4e9b94725db4891a4666
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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