(S)-N-Benzylglutamic acid → (S)-1-Benzyl-5-carboxy-2-pyrrolidinone

HRID 743901Notes

Reaction equation

HRID 743901 reaction equation
[CH2:1]([NH:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@H:9]1[C:15]([OH:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 11107380(S)-N-Benzylglutamic acid

Product 1

HCID 10900113(S)-1-Benzyl-5-carboxy-2-pyrrolidinoneYield 98.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Benzyl-glutamic acid (35 g) was dissolved in 300 ml of water and refluxed for 15 hours. The solution was extracted with methylene chloride, washed with brine, dried over sodium sulfate and concentrated to yield 32 g of N-benzyl-5-oxo-proline. The acid (55.25 mmoles, 12.1 g) was dissolved in 15 ml of DMF and 30 ml acetonitrile. The solution was cooled to -25° C. Oxalyl chloride (5.0 ml) in 10 ml acetonitrile was added. The solution was stirred vigorously for 30 minutes. A solution of t-butanol (135 mmoles, 10.0 g) and pyridine (13.2 g) in 10 ml acetonitrile was added over 30 minutes and then warmed to 0° C. Brine and ethyl acetate were added. The organic phase was diluted and washed with water, dried and concentrated to yield 10.7 g of N-benzyl-5-oxo-L-proline t-butyl ester. (MS)

Workup

  1. temperaturerefluxed for 15 hours
  2. extractionThe solution was extracted with methylene chloride
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-524e94e891e14a8c892d4aa4b0237283
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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