2-Bromopropionic acid → HCID 53651654, compound

HRID 2418412Notes

Reaction equation

HRID 2418412 reaction equation
Cl.[NH2:2][C@H:3]([C:5]([O:7][CH3:8])=[O:6])[CH3:4].Br[CH:10]([CH3:14])[C:11]([OH:13])=[O:12].[OH-].[Na+]>O1CCOCC1.O>[C:5]([CH:3]([NH:2][C@H:10]([C:11]([OH:13])=[O:12])[CH3:14])[CH3:4])([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 117292-Bromopropionic acidHCID 14798Sodium Hydroxide2×HCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 53651654HCID 53651654, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Neutralize a solution of 1.4 g of methyl L-alaninate HCl and 3.1 g of α-bromopropionic acid in a dioxane-water mixture to pH 9 with sodium hydroxide. Warm to 70° and hold for 30 minutes, keeping the pH at 8 to 9 by addition of sodium hydroxide as necessary. Cool, apply to a column of Dowex 50 (H+) ion exchange resin, wash with water, and elute with 2% pyridine in water. Combine the product fractions and freeze dry. Purify this crude by chromatography on an ion-exchange column of Dowex 50 (Na+) in 0.5M sodium citrate buffer pH 3.3. Collect the product fractions, concentrate to a small volume in vacuo, and repeat the Dowex 50 (H+) chromatography. Freeze dry the product fractions to obtain the pure N-(1-carbomethoxyethyl)-alanine.

Workup

  1. temperatureWarm to 70°
  2. temperatureCool, apply to a column of Dowex 50 (H+) ion exchange resin
  3. washwash with water
  4. washelute with 2% pyridine in water
  5. customdry
  6. customPurify this crude by chromatography on an ion-exchange column of Dowex 50 (Na+) in 0.5M sodium citrate buffer pH 3.3
  7. customCollect the product fractions
  8. concentrationconcentrate to a small volume in vacuo
  9. customFreeze dry the product fractions

Sources & evidence

ORD record
ord-9e862fd875e24f2b8d400f4b5a6efbf4
Source dataset
uspto-grants-1984_09
Patent number
US04472380

Reaction notes

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