Sodium Hydroxide → HCID 69509116, compound

HRID 1354057Notes

Reaction equation

HRID 1354057 reaction equation
C([O:3][C:4](=[O:41])[CH2:5][C@@H:6]([NH:19][C:20]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])=[CH:24][N:23]=[C:22]([N:33]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH3:34])[N:21]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO.O>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:25]1[C:20]([NH:19][C@@H:6]([C:7]2[CH:8]=[CH:9][C:10]([O:13][C:14]([N:16]([CH3:17])[CH3:18])=[O:15])=[CH:11][CH:12]=2)[CH2:5][C:4]([OH:41])=[O:3])=[N:21][C:22]([N:33]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH3:34])=[N:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69508929HCID 69508929, compound

Product 1

HCID 69509116HCID 69509116, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
22 °C

Procedure

To a solution of (R)-3-(5-(2-fluorophenyl)-2-(N-cyclohexyl-N-methylamino)pyrimidin-4-ylamino)-3-(4-(dimethylaminocarbonyl)oxyphenyl)propanoic acid ethyl ester (1.0 eq) in 3:1 MeOH/H2O was added 1M NaOH (2.5 eq). The mixture was stirred at 22° C. for 6 hr, and then the MeOH and H2O were evaporated. The residue was partitioned between Et2O and H2O, and then the separated aqueous layer was acidified to pH=3 by addition of 0.1 M H3PO4. The aqueous layer was extracted three times with 3:1 CHCl3/iPrOH, and then the CHCl3/iPrOH extracts were treated with MgSO4, filtered and evaporated to give (R)-3-(5-(2-fluorophenyl)-2-(N-cyclohexyl-N-methylamino)pyrimidin-4-ylamino)-3-(4-(dimethylaminocarbonyl)oxyphenyl)propanoic acid.

Workup

  1. customthe MeOH and H2O were evaporated
  2. customThe residue was partitioned between Et2O and H2O
  3. additionthe separated aqueous layer was acidified to pH=3 by addition of 0.1 M H3PO4
  4. extractionThe aqueous layer was extracted three times with 3:1 CHCl3/iPrOH
  5. additionthe CHCl3/iPrOH extracts were treated with MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-45b58dbda7094405821806288a2c771d
Source dataset
uspto-grants-2007_05
Patent number
US07223762B2

Reaction notes

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