Sodium Hydroxide → HCID 178508861, compound

HRID 543889Notes

Reaction equation

HRID 543889 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][N:14]([CH2:33][CH2:34][F:35])[C:15]3[CH:32]=[CH:31][C:18]([C:19]([NH:21][C@H:22]([C:28]([O-:30])=[O:29])[CH2:23][CH2:24][C:25]([O-:27])=[O:26])=[O:20])=[CH:17][CH:16]=3)[CH:8]=2)[N:3]=1.[OH-].[Na+]>O.C(O)C>[NH2:1][C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][N:14]([CH2:33][CH2:34][F:35])[C:15]3[CH:16]=[CH:17][C:18]([C:19]([NH:21][C@H:22]([C:28]([OH:30])=[O:29])[CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:20])=[CH:31][CH:32]=3)[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178508860HCID 178508860, compound

Product 1

HCID 178508861HCID 178508861, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-(4-(N-((2-amino-4-hydroxy-6-quinazolinyl)methyl)2-fluoroethylamino)benzoyl)-L-glutamate (0.206 g) was suspended in a mixture of water (4.5 ml) and ethanol (1 ml) and treated with 1 N NaOH aq. (5 mol eq.). Vigorous shaking gave a solution within 5 min. After 2 hr. the solution was clarified by filtration and the pH brought to 4.0 using 1 N HCl aq. A gelatinous precipitate of the product resulted. It was freed from inorganic ions by three cycles of suspension-centrifugation-decantation. The amorphous white solid was dried at 70° C. in vacuo, (m.p.>350° C. with some darkening and slow decomposition from 245° C.) giving N-(4-(N-((2-amino-4-hydroxy-6-quinazolinyl)methyl)2-fluoroethylamino)benzoyl)-L-glutamic acid (CB 3731). Yield 60.1%. The structure was confirmed by elemental analysis (C,H,N and F) and by uv spectroscopy (spectrum determined in 0.1 N NaOH aq.). uv λ(nm) (ε) maxima: 307 (29,200), 275 (19,500), 227.5 (49,700 ); minima: 279 (19,200), 250 (9,100).

Workup

  1. customgave a solution within 5 min
  2. filtrationthe solution was clarified by filtration
  3. customresulted
  4. customThe amorphous white solid was dried at 70° C. in vacuo

Sources & evidence

ORD record
ord-5bb2b441fda24c91b894843f4e1159d3
Source dataset
uspto-grants-1984_05
Patent number
US04447608

Reaction notes

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