Triethylamine → Ethyl 3-{[(benzyloxy)carbonyl]amino}propanoate

HRID 17426

Reaction equation

HRID 17426 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].C(N(CC)CC)C>ClCCl>[CH2:14]([O:13][C:11]([NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 12116647Ethyl 3-{[(benzyloxy)carbonyl]amino}propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-aminopropionate hydrochloride (2.00 g, 13.0 mmol) was dissolved in dichloromethane (40 ml), and benzyl chloroformate (2.00 ml, 14.1 mmol) was added. With cooling with ice, triethylamine (4.00 ml, 28.9 mmol) was added, followed by stirring at room temperature for 15 hours, then the reaction, liquid was concentrated. Ethyl acetate and water were added, the organic layer was collected, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, the resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70:1) to obtain a pale yellow oil (3.26 g, quant).

Workup

  1. additionwas added
  2. customthe reaction, liquid
  3. concentrationwas concentrated
  4. additionEthyl acetate and water were added
  5. customthe organic layer was collected
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70:1)
  9. customto obtain a pale yellow oil (3.26 g, quant)

Sources & evidence

ORD record
ord-264e2d6a7e9b4546809255c18b4318aa
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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