Sodium Hydroxide → HCID 13478339, compound

HRID 371464Notes

Reaction equation

HRID 371464 reaction equation
C([O:3][C:4](=[O:38])[C@H:5]([CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])[NH:6][C:7](=[O:30])[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:21]([NH2:29])=[N:22][C:23]([NH2:28])=[N:24][C:25]=3[CH2:26][CH3:27])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)C.[OH-].[Na+]>CO>[NH2:28][C:23]1[N:22]=[C:21]([NH2:29])[C:20]([N:17]2[CH2:16][CH2:15][N:14]([C:11]3[CH:10]=[CH:9][C:8]([C:7]([NH:6][C@H:5]([C:4]([OH:38])=[O:3])[CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])=[CH:13][CH:12]=3)[CH2:19][CH2:18]2)=[C:25]([CH2:26][CH3:27])[N:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13478340HCID 13478340, compound

Product 1

HCID 13478339HCID 13478339, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.0 g (3.85 mmole) of N-[4-[4-(2,4-diamino-6-ethyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-L-glutamic acid diethyl ester and 0.6 g (7.70 mmole) of a 50% aqueous sodium hydroxide solution in 100 ml of methanol was stirred at room temperature for 16 hours. Methanol was removed in vacuo below 23° C. The residue was dissolved in 50 ml of ice water and filtered. The filtrate was acidified with citric acid to pH 5. The solid precipitate was collected, washed with water, and triturated with boiling ethanol. After drying in vacuo at 67° for 16 hours, 1.3 g of the product was obtained as a white powder; mp 275° C. (with decomposition).

Workup

  1. customMethanol was removed in vacuo below 23° C
  2. dissolutionThe residue was dissolved in 50 ml of ice water
  3. filtrationfiltered
  4. customThe solid precipitate was collected
  5. washwashed with water
  6. customtriturated with boiling ethanol
  7. customAfter drying in vacuo at 67° for 16 hours

Sources & evidence

ORD record
ord-4bf6417f16a04b20baa69d27748cd26c
Source dataset
uspto-grants-1985_07
Patent number
US04532240

Reaction notes

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