Benzyl chloroformate → 3-{[(benzyloxy)carbonyl]amino}butanoic acid

HRID 517288Notes

Reaction equation

HRID 517288 reaction equation
[NH2:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[K+].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>O>[CH2:14]([O:13][C:11]([NH:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 10932Beta-Aminobutyric AcidHCID 14797Potassium Hydroxide

Product 1

HCID 3042803-{[(benzyloxy)carbonyl]amino}butanoic acidYield 44.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

Into a 2000-mL 4-necked round-bottom flask was placed a solution of 3-aminobutanoic acid (100 g, 969.75 mmol, 1.00 equiv) in water (1000 mL), followed by the addition of potassium hydroxide (136 g, 2.42 mol, 2.50 equiv) in several batches. To this was added benzyl chloroformate (247 g, 1.45 mol, 1.50 equiv) dropwise with stirring at 0-5° C. The resulting solution was stirred at 25° C. for 5 h. The reaction progress was monitored by LCMS. The resulting solution was extracted with 3×250 mL of dichloromethane and the aqueous layers were combined. The pH value of the water phase was adjusted to 3 with hydrogen chloride (2 mol/L). The precipitates were collected by filtration and dried to afford 102 g (44%) of 3-[[(benzyloxy)carbonyl]amino]butanoic acid as a white solid.

Workup

  1. customInto a 2000-mL 4-necked round-bottom flask was placed
  2. stirringThe resulting solution was stirred at 25° C. for 5 h
  3. extractionThe resulting solution was extracted with 3×250 mL of dichloromethane
  4. filtrationThe precipitates were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-38e4140eddf247258f00ba2e2394d3e3
Source dataset
uspto-grants-2015_08
Patent number
US09115101B2

Reaction notes

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