Triethylamine → HCID 57440707, compound

HRID 2102359Notes

Reaction equation

HRID 2102359 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6].C(N(CC)CC)C.[C:16](Cl)(=[O:19])[CH2:17][CH3:18]>ClCCl>[C:16]([NH:6][C@@H:5]([CH3:7])[C:4]([O:3][CH3:2])=[O:8])(=[O:19])[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 2733257Alanine methyl ester hydrochloride

Product 1

HCID 57440707HCID 57440707, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-Alanine methyl ester hydrochloride salt (14 g, 0.1 mol) was dissolved in dichloromethane (150 mL) and treated with triethylamine (30.45 g, 0.3 mmol). The solution was stirred and propionyl chloride added dropwise. After stirring overnight the mixture was quenched by addition of 1M hydrochloric acid (200 mL) and the organic layer separated. The aqueous layer was re-extracted with dichloromethane (3×200 mL) and the combined organic layers were dried with magnesium sulfate, filtered and evaporated to a to a clear oil (16.0 g, quant.).

Workup

  1. stirringAfter stirring overnight the mixture
  2. customwas quenched by addition of 1M hydrochloric acid (200 mL)
  3. customthe organic layer separated
  4. extractionThe aqueous layer was re-extracted with dichloromethane (3×200 mL)
  5. dry with materialthe combined organic layers were dried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to a to a clear oil (16.0 g, quant.)

Sources & evidence

ORD record
ord-0fa4a483fbdb43039b856e459d60ec72
Source dataset
uspto-grants-2009_08
Patent number
US07576081B2

Reaction notes

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