Hydrochloric Acid → L-Threonine, N-[(phenylmethoxy)carbonyl]-

HRID 1796804Notes

Reaction equation

HRID 1796804 reaction equation
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[C@H:3]([CH3:5])[OH:4].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].Cl>O>[CH2:13]([O:12][C:10]([NH:1][CH:2]([CH:3]([OH:4])[CH3:5])[C:6]([OH:8])=[O:7])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 69435D-Threonine

Product 1

HCID 433607L-Threonine, N-[(phenylmethoxy)carbonyl]-Yield 102.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of D-threonine (50.7 g, 0.426 mol) in water (800 ml) at about 0° C. was added benzyl chloroformate (66 ml, 0.462 mol) dropwise over about 15 minutes. The reaction was allowed to warm to about 23° C. and was stirred at that temperature for about 18 hours. The reaction was cooled with ice and acidified with concentrated hydrochloric acid, extracted with ether (3 times) and the organic layers were concentrated to give 110.9 g of 2-benzyloxycarbonylamino-3-hydroxy-butyric acid as a colorless oil.

Workup

  1. temperatureThe reaction was cooled with ice
  2. extractionextracted with ether (3 times)
  3. concentrationthe organic layers were concentrated

Sources & evidence

ORD record
ord-7a28df36ef6a46ae9ead9b9a701d3c40
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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