Hydrochloric Acid → HCID 2929886, compound

HRID 860595Notes

Reaction equation

HRID 860595 reaction equation
C[O:2][C:3](=[O:19])[CH:4]([NH:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=1)[CH3:5].[OH-].[Na+].Cl>O1CCCC1>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH:4]([CH3:5])[C:3]([OH:19])=[O:2])=[O:18])=[CH:9][CH:10]=1)([CH3:16])([CH3:15])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2918890HCID 2918890, compound

Product 1

HCID 2929886HCID 2929886, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-tert-Butyl-benzoylamino)-propionic acid methyl ester (26.3 g, 95.6 mmol), 200 mL 1M sodium hydroxide, and 100 mL tetrahydrofuran is stirred at room temperature 20 hr. The resulting clear solution is cooled on an ice/water bath and the pH is adjusted to 2 with concentrated hydrochloric acid. The product is extracted with three 250 mL portions of ethyl acetate. The combined extracts are washed with 100 mL each of water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford 2-(4-tert-Butyl-benzoylamino)-propionic acid as a white solid, 24.6 g, 95%. MS M++1 260.

Workup

  1. temperatureThe resulting clear solution is cooled on an ice/water bath
  2. extractionThe product is extracted with three 250 mL portions of ethyl acetate
  3. washThe combined extracts are washed with 100 mL each of water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-43cd7b432e714497b6f01113340a6f6c
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

Loading…