Ammonium Hydroxide → 2-Amino-3-(3,5-difluorophenyl)propanamide

HRID 714281Notes

Reaction equation

HRID 714281 reaction equation
Cl.[NH2:2][CH:3]([CH2:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)[C:4](OC)=[O:5].[OH-].[NH4+:18]>O>[NH2:2][CH:3]([CH2:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)[C:4]([NH2:18])=[O:5]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 66940454Methyl 2-amino-3-(3,5-difluorophenyl)propanoate hydrochloride

Product 1

HCID 582479162-Amino-3-(3,5-difluorophenyl)propanamideYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 2-amino-3-(3,5-difluorophenyl)propanoate hydrochloride (3.67 g, 14.6 mmol) in aqueous ammonium hydroxide (5.5 mL) and water (22 mL) was stirred at ambient temperature for 18 hours and extracted with dichloromethane (4×50 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to dryness to give 2-amino-3-(3,5-difluorophenyl)propanamide as a colorless solid (1.50 g, 51%): 1H NMR (300 MHz, CD3OD) δ 6.92-6.75 (m, 3H), 3.56 (dd, J=7.3, 6.3 Hz, 1H), 3.00 (dd, J=13.4, 6.3 Hz, 1H), 2.83 (dd, J=13.4, 7.4 Hz, 1H).

Workup

  1. extractionextracted with dichloromethane (4×50 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-70da7fb7abe64045882a4d8c925bee8c
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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