Sodium Hydroxide → HCID 53912996, compound

HRID 1904022Notes

Reaction equation

HRID 1904022 reaction equation
C([O:3][C:4]([CH:6]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C@H:16]([C:22]([OH:24])=[O:23])[CH2:17][CH2:18][C:19](=[O:21])[NH2:20])=[CH:11][CH:10]=1)[CH2:7][CH3:8])=[O:5])C.[OH-].[Na+]>CO.O>[C:4]([CH:6]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][C@H:16]([C:22]([OH:24])=[O:23])[CH2:17][CH2:18][C:19](=[O:21])[NH2:20])=[CH:13][CH:14]=1)[CH2:7][CH3:8])([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13255339HCID 13255339, compound

Product 1

HCID 53912996HCID 53912996, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In 10 ml of methanol was suspended 1.68 g (0.005 mole) of N-[4-(1-ethoxycarbonyl-n-propyl)phenyl]-L-glutamine and a solution of 0.42 g of sodium hydroxide in 20 ml of water was added thereto and stirred for 1.5 hours at room temperature. The solvent was then distilled off in vacuo to about a half volume and the remaining solution was acidified to pH 4 with 5% hydrochloric acid. The precipitated crystals were collected by filtration, washed with cold water and dried in vacuo to give 1.16 g (0.0038 mole, 75% yield) of N-[4-(1-carboxy-n-propyl)phenyl]-L-glutamine, m.p. 166.5°-167.0° C.

Workup

  1. distillationThe solvent was then distilled off in vacuo to about a half volume
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with cold water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dbccac1a9a05454a904c5bddee1cf130
Source dataset
uspto-grants-1984_03
Patent number
US04439448

Reaction notes

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