Water → HCID 22875200, compound

HRID 267087Notes

Reaction equation

HRID 267087 reaction equation
C[O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][CH2:7][C:6](=[O:9])[N:5]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.[OH-].[Na+].O>CO>[N+:17]([C:14]1[CH:13]=[CH:12][C:11]([CH2:10][N:5]2[C:6](=[O:9])[CH2:7][CH2:8][C@H:4]2[C:3]([OH:20])=[O:2])=[CH:16][CH:15]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15288189HCID 15288189, compound

Product 1

HCID 22875200HCID 22875200, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(S)-N-(4-Nitrobenzyl)pyroglutamic acid methyl ester (0.365 g, 1.31 mmol) was dissolved in 10 ml MeOH, cooled to 0° C., and 1N NaOH (5.2 ml, 5.2 mmol) was added. The reaction was stirred at room temperature for 1 h. Water (50 ml) was added and the aqueous was washed with 2×50 ml EtOAc. The aqueous was acidified with 1N HCl and extracted with 3×40 ml EtOAc. The organic layers were dried (MgSO4), filtered, and concentrated to give the title compound as a solid.

Workup

  1. washthe aqueous was washed with 2×50 ml EtOAc
  2. extractionextracted with 3×40 ml EtOAc
  3. dry with materialThe organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5943a59d9f584d82b95d692ece8b1737
Source dataset
uspto-grants-1997_07
Patent number
US05652257

Reaction notes

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