Sodium Hydroxide → (R)-3-[(E)-3-(5-cyano-2-methoxy-phenyl)-acryloylamino]-4-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-butyric acid

HRID 1797265Notes

Reaction equation

HRID 1797265 reaction equation
C([O:8][C:9](=[O:42])[CH2:10][C@@H:11]([NH:27][C:28](=[O:41])/[CH:29]=[CH:30]/[C:31]1[CH:36]=[C:35]([C:37]#[N:38])[CH:34]=[CH:33][C:32]=1[O:39][CH3:40])[CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)C1C=CC=CC=1.[OH-].[Na+]>CO>[C:37]([C:35]1[CH:34]=[CH:33][C:32]([O:39][CH3:40])=[C:31](/[CH:30]=[CH:29]/[C:28]([NH:27][C@@H:11]([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH2:10][C:9]([OH:42])=[O:8])=[O:41])[CH:36]=1)#[N:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68575706(R)-3-[(E)-3-(5-cyano-2-methoxy-phenyl)-acryloylamino]-4-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-butyric acid benzyl ester

Product 1

HCID 10140715(R)-3-[(E)-3-(5-cyano-2-methoxy-phenyl)-acryloylamino]-4-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-butyric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R)-3-[(E)-3-(5-cyano-2-methoxy-phenyl)-acryloylamino]-4-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-butyric acid benzyl ester (1.43 g, 2.52 mmol) in methanol (15 ml) is treated with NaOH solution, (2.5 ml, 4M). The reaction mixture is stirred at ambient temperature for 1 hour. The methanol is evaporated and the resulting aqueous solution diluted with water and washed with diethyl ether. The aqueous phase is neutralised with 1N HCl solution and extracted into isopropanol/chloroform (1:3). The organic phase is evaporated and dried under high vacuum to afford (R)-3-[(E)-3-(5-cyano-2-methoxy-phenyl)-acryloylamino]-4-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-butyric acid. [MH]+ 482.1.

Workup

  1. customThe methanol is evaporated
  2. additionthe resulting aqueous solution diluted with water
  3. washwashed with diethyl ether
  4. extractionextracted into isopropanol/chloroform (1:3)
  5. customThe organic phase is evaporated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-757478942d144b68a5331ad5c7824d02
Source dataset
uspto-grants-2006_04
Patent number
US07034042B2

Reaction notes

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