Benzyl chloroformate → L-Glutamic acid, N-((phenylmethoxy)carbonyl)-

HRID 990026Notes

Reaction equation

HRID 990026 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[OH-].[Na+].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>O>[C:18]1([CH2:17][O:16][C:14]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:15])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 33032L-Glutamic Acid

Product 1

HCID 70866L-Glutamic acid, N-((phenylmethoxy)carbonyl)-Yield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of L-glutamic acid (23.5 g; 160 mmol) in H2O (100 mL) was stirred, maintaining the pH at 8.5 with 10 M NaOH until complete dissolution. Benzyl chloroformate (35 g; 205 mmol) was added over 15 min to the clear solution. The mixture was stirred, maintaining the pH at 9 by adding 10 M NaOH until the reaction was complete. The cloudy mixture was washed with Et2O (3×150 mL) and then the pH of the resulting solution was adjusted to 2.1 with 1 M HCl. The cloudy aqueous mixture was extracted with Et2O (2×200 mL), the organic layers were collected and evaporated to yield the desired product (39.13 g; 139 mmol). Yield 87%.

Workup

  1. dissolutionuntil complete dissolution
  2. stirringThe mixture was stirred
  3. temperaturemaintaining the pH at 9
  4. washThe cloudy mixture was washed with Et2O (3×150 mL)
  5. extractionThe cloudy aqueous mixture was extracted with Et2O (2×200 mL)
  6. customthe organic layers were collected
  7. customevaporated

Sources & evidence

ORD record
ord-f37b47dac080400d93925f3a54f55e72
Source dataset
uspto-grants-2002_10
Patent number
US06458337B1

Reaction notes

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