Sodium Hydroxide → HCID 23146023, compound

HRID 1051749Notes

Reaction equation

HRID 1051749 reaction equation
[NH2:1][CH:2]([CH2:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[F:17])[CH2:3][C:4]([O:6]C)=[O:5].O=C(CC1C=C(F)C(F)=CC=1F)CC(OC)=O.[OH-].[Na+]>CO.O>[NH2:1][CH:2]([CH2:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[F:17])[CH2:3][C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 29942605Methyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoateHCID 49820754Methyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate

Product 1

HCID 23146023HCID 23146023, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate (5.8 g, 23.5 mmol), prepared from methyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate according to the process of WO 10/122578, was refluxed in the solution of NaOH (1.88 g, 46.9 mmol) in MeOH (40 mL) and water (20 mL) overnight. After the completion of the reaction, the MeOH was evaporated and 80 mL of water was added. The pH of the solution was adjusted to 8 by addition of 6M HCl and the resulting white precipitate was filtered off and dried overnight in an oven at 100° C. to afford 3.5 g of (±)-Ia.

Workup

  1. customAfter the completion of the reaction
  2. customthe MeOH was evaporated
  3. addition80 mL of water was added
  4. additionThe pH of the solution was adjusted to 8 by addition of 6M HCl
  5. filtrationthe resulting white precipitate was filtered off
  6. customdried overnight in an oven at 100° C.
  7. customto afford 3.5 g of (±)-Ia

Sources & evidence

ORD record
ord-265c6eecd1ea4571bded44d36b125f31
Source dataset
uspto-grants-2016_07
Patent number
US09388188B2

Reaction notes

Loading…