Sodium Hydroxide → HCID 67090018, compound

HRID 2074418Notes

Reaction equation

HRID 2074418 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([C:6]([NH:8][CH:9]([CH3:35])[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH3:30])[C:25]=4[O:28][CH3:29])[CH:20]([CH2:31][NH:32]C=O)[O:19]3)[CH2:14][CH2:13]2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[NH2:32][CH2:31][C@H:20]1[C:21]2[C:26](=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][CH:22]=2)[CH2:27][C@@H:18]([CH:15]2[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[C:5]3[CH:36]=[CH:37][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH3:35])[CH2:13][CH2:14]2)[O:19]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86612288HCID 86612288, compound

Product 1

HCID 67090018HCID 67090018, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Stir and heat at 70° C. a solution of 4-chloro-N-{3-[4-(1-formylaminomethyl-5-methoxy-6-methyl-isochroman-3-yl)-piperidin-1-yl]-1-methylpropyl}-benzamide in CH3OH/THF (10 mL of 1:1 solution) and of 15% NaOH solution (2 mL) for 4 hours. Concentrate the reaction mixture, and extract three times with EtOAc (2 mL). Wash the combined organic phase sequentially with H2O (2 mL), brine (2 mL), and then dry over MgSO4. Concentrate and purify the crude product on a 2 g SCX column.

Workup

  1. concentrationConcentrate the reaction mixture
  2. extractionextract three times with EtOAc (2 mL)
  3. washWash the combined organic phase sequentially with H2O (2 mL), brine (2 mL)
  4. dry with materialdry over MgSO4
  5. concentrationConcentrate
  6. custompurify the crude product on a 2 g SCX column

Sources & evidence

ORD record
ord-c40dcc64ec5c4d6094717f9296b2643d
Source dataset
uspto-grants-2011_04
Patent number
US07919508B2

Reaction notes

Loading…