Methyl 4-tert-butyl-2-hydroxybenzoate → Methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-tert-butylbenzoate

HRID 644286Notes

Reaction equation

HRID 644286 reaction equation
C(O[CH2:6][C:7]([CH3:28])([CH3:27])[CH:8](N=C=O)[O:9][C:10]1[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])(C)(C)C.C(C1C=C(O)C(=CC=1)C(OC)=O)(C)(C)C.[C:44]([O:48][C:49]([NH:51]CC(C)(C)CO)=[O:50])([CH3:47])([CH3:46])[CH3:45]>>[C:44]([O:48][C:49]([NH:51][CH2:6][C:7]([CH3:28])([CH3:27])[CH2:8][O:9][C:10]1[CH:19]=[C:18]([C:20]([CH3:22])([CH3:23])[CH3:21])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[O:50])([CH3:47])([CH3:46])[CH3:45]

Participants

4

Reactant 3

HCID 20777194Methyl 4-tert-butyl-2-hydroxybenzoateHCID 21263232tert-butyl N-(3-hydroxy-2,2-dimethylpropyl)carbamateHCID 86634215Methyl 2-(3-tert-butoxy-carbonylamino-2,2-dimethylpropoxy)-4-(tert-butyl)benzoate

Product 1

HCID 68530988Methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-tert-butylbenzoate

Procedure

Using methods substantially equivalent to Example 21-C, except that the Mitsonobu reaction was allowed to proceed for 7 to 10 days, methyl 2-(3-tert-butoxy-carbonylamino-2,2-dimethylpropoxy)-4-(tert-butyl)benzoate (10.85 g, 39%) as a pale yellow brittle foam was prepared from methyl 4-(tert-butyl)salicylate (14.72 g, 70.8 mmol) and 3-(tert-butoxycarbonylamino)-2,2-dimethylpropanol (14.37 g, 70.8 mmol).

Workup

  1. customexcept that the Mitsonobu reaction

Sources & evidence

ORD record
ord-1afff3bbd0494bb2bc7b22f384b78582
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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