Potassium Hydroxide → HCID 11465546, compound

HRID 1058180Notes

Reaction equation

HRID 1058180 reaction equation
COC([NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[P:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27])=O.[OH-].[K+]>CO>[NH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[P:26]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:27]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11272493HCID 11272493, compound

Product 1

HCID 11465546HCID 11465546, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

8.01 gram (15.2 mmol) of (−)-2-methoxycarbonylamino-2′-diphenylphosphinyl-1,1′-binaphthyl (the formula (1-2b-1)) was dissolved in 304 ml of methanol. To the solution, 152 ml of 40 percent aqueous solution of potassium hydroxide was added dropwise over 30 minutes and then stirred at 95° C. for 2 hours. The resultant mixture was extracted with 300 ml of ethyl acetate, and the extract was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the residue was purified using a silica gel column chromatography (eluent: ethyl acetate) to obtain 7.16 gram of the titled compound.

Workup

  1. extractionThe resultant mixture was extracted with 300 ml of ethyl acetate
  2. washthe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under a reduced pressure
  5. customthe residue was purified

Sources & evidence

ORD record
ord-8f776da149134ac4820f14c98ae7bd11
Source dataset
uspto-grants-2003_02
Patent number
US06515156B2

Reaction notes

Loading…