Sodium Hydroxide → HCID 11716723, compound

HRID 1454106Notes

Reaction equation

HRID 1454106 reaction equation
[OH-].[Na+].[NH2:3][C:4](=[O:17])[CH2:5][CH:6]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[C:7]([OH:9])=[O:8].[CH:18]1([CH2:24][CH2:25]Br)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C>[NH2:3][C:4](=[O:17])[CH2:5][CH:6]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:25][CH2:24][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:15]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15440(2-Bromoethyl)cyclohexaneHCID 68833440HCID 68833440, compound

Product 1

HCID 11716723HCID 11716723, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous sodium hydroxide solution (2.0 M; 50 μL, 100 μmol) was added in one portion to a stirred solution of 4-amino-2-(4-hydroxyphenyl)-4-oxobutanoic acid (10 mg, 47 μmol) in ethanol (1 mL) at room temperature. After stirring for 10 min cyclohexylethylbromide (9.0 mg, 47 μmol) was added and the resulting mixture heated at reflux for 12 h. On cooling to room temperature the volatiles were evaporated and the residue purified by mass directed auto-preparative reverse phase HPLC to give the title compound as a white solid (2.1 mg, 14%). LC/MS: 3.34 min; z/e 320, calcd (M+1) 320. 1H NMR (400 MHz: MeOD): 7.20 (2H), 6.85 (2H), 4.00 (3H), 2.95 (1H), 2.55 (1H), 1.70 (6H), 1.50 (1H), 1.25 (4H), 0.92 (2H). The absolute regiochemistry of the product was unambiguously assigned using an HMBC correlation experiment.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture heated
  3. temperatureat reflux for 12 h
  4. customwere evaporated
  5. customthe residue purified by mass

Sources & evidence

ORD record
ord-3e81f32cf6d048b7a739611ca08d23ba
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

Loading…