Sodium Hydroxide → (2-{[5-(2-Hydroxy-ethyl)-benzofuran-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester

HRID 1271874Notes

Reaction equation

HRID 1271874 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([CH:26]=[CH2:27])=[CH:22][C:20]=2[CH:21]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2].B1C2CCCC1CCC2.[OH-:38].[Na+]>C1COCC1.O>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][OH:38])=[CH:22][C:20]=2[CH:21]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 69490024{2-[(5-Vinyl-benzofuran-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 69487867(2-{[5-(2-Hydroxy-ethyl)-benzofuran-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl esterYield 6.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 114 mg (o.30 mmol) {2-[(5-Vinyl-benzofuran-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (57), 5 ml THF and 1.4 ml of a 0.5M solution of 9-BBN in THF was stirred at rt for 4 h. A solution of 86 mg NaOH in 0.6 ml water was added and stirring was continued for further 2 h. The reaction mixture was washed with brine and the organic phase dried over sodium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (petrolether/ethylacetate 1:1) to give 54 mg (0.136 mmol) (2-{[5-(2-Hydroxy-ethyl)-benzofuran-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester (58).

Workup

  1. washThe reaction mixture was washed with brine
  2. dry with materialthe organic phase dried over sodium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-66b2057567004a7fbd62dbb552eade47
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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