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

HRID 965335

Reaction equation

HRID 965335 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[OH-].[Na+].[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1.O>[CH2:12]([O:19][C:20]([NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-aminopropionate hydrochloride (10 g) was dissolved in a mixture of tetrahydrofuran (100 ml) and water, which was cooled at 0° to 5° C. in an ice bath and adjusted to pH 8.2 with 30% aqueous sodium hydroxide solution. To a resulting solution was added with care benzyloxycarbonyl chloride (10.3 ml), with maintaining the pH from pH 8.0 to 9.0 with 30% aqueous sodium hydroxide solution at 0° to 5° C. The reaction mixture was extracted with ethyl acetate (300 ml) and organic layer was separated, which was washed two times with saturated sodium chloride in water and dried over magnesium sulfate. Solvent was removed under reduced pressure to give ethyl 3-(benzyloxycarbonylamino)-propionate (15.3 g).

Workup

  1. temperaturewas cooled at 0° to 5° C. in an ice bath
  2. extractionThe reaction mixture was extracted with ethyl acetate (300 ml) and organic layer
  3. customwas separated
  4. washwhich was washed two times with saturated sodium chloride in water
  5. dry with materialdried over magnesium sulfate
  6. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b5f446095697466692242d5efe51023c
Source dataset
uspto-grants-1998_06
Patent number
US05773530

Linked notes

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