Water → HCID 5712185, compound

HRID 982163Notes

Reaction equation

HRID 982163 reaction equation
[OH-].[Na+].O.[NH2:4][C@H:5]([C:7]([OH:9])=[O:8])[CH3:6].[Cl:10][CH2:11][C:12](Cl)=[O:13]>C(OCC)C>[Cl:10][CH2:11][C:12]([NH:4][C@H:5]([C:7]([OH:9])=[O:8])[CH3:6])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 5950L-AlanineHCID 6577Chloroacetyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 5712185HCID 5712185, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Into a 5-liter, 4-neck, round-bottom flask equipped with a mechanical stirrer, pH probe, thermometer, two 1-liter addition funnels and a nitrogen bubble were charged 157 g (3.93 mole) of sodium hydroxide and 1800 ml of water followed by 350 g (3.93 mole) of L-alanine. After all the solids dissolved, 600 ml of diethyl ether was added and solutions of chloroacetyl chloride (500 g, 4.43 mole) in 600 ml of diethyl ether and dilute sodium hydroxide (225 g in 500 ml water) were added concomitantly while maintaining the pH at about 11 and the temperature at about 0° C. by external cooling. The resulting mixture was allowed to warm to room temperature, and the ether layer separated. The aqueous layer was acidified with concentrated hydrochloric acid to pH 1 and extracted with four 1-liter portions of ethyl acetate. The combined organic extract was dried over anhydrous magnesium sulfate and rotoevaporated to yield 550 g (85%) of 2-chloroacetyl-(L)-alanine as a white crystalline solid, melting point (mp) 93°-96° C. This material can be purified by recrystallization from ethyl acetate, but this is not necessary for the next step.

Workup

  1. customInto a 5-liter, 4-neck, round-bottom flask equipped with a mechanical stirrer
  2. customa nitrogen bubble
  3. dissolutionAfter all the solids dissolved
  4. temperaturewhile maintaining the pH at about 11
  5. customat about 0° C.
  6. customthe ether layer separated
  7. extractionextracted with four 1-liter portions of ethyl acetate
  8. extractionThe combined organic extract
  9. dry with materialwas dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-23fe5f611e844d2cb448f1eb06a53c04
Source dataset
uspto-grants-1991_02
Patent number
US04994551

Reaction notes

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