Water → (S)-2-(4-(((4-oxo-3,4-dihydroquinazolin-6-yl)methyl)(prop-2-ynyl)amino)benzamido)pentanedioic acid

HRID 2254570Notes

Reaction equation

HRID 2254570 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]([CH2:36][C:37]#[CH:38])[C:14]3[CH:35]=[CH:34][C:17]([C:18]([NH:20][C@H:21]([C:29]([O:31]CC)=[O:30])[CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:19])=[CH:16][CH:15]=3)[CH:10]=2)[N:5]=[CH:4][N:3]1COC(=O)C(C)(C)C.O>CCO>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]([CH2:36][C:37]#[CH:38])[C:14]3[CH:15]=[CH:16][C:17]([C:18]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:19])=[CH:34][CH:35]=3)[CH:10]=2)[N:5]=[CH:4][NH:3]1

Participants

4

Reactant 2

HCID 962WaterHCID 13691215Diethyl N-(4-(N-((3,4-dihydro-4-oxo-3-((pivaloyl)oxy) methyl-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-L-glutamate

Product 1

HCID 136056561(S)-2-(4-(((4-oxo-3,4-dihydroquinazolin-6-yl)methyl)(prop-2-ynyl)amino)benzamido)pentanedioic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the gummy triester (5)(0.633 g, 0.001 mole), H2O (18 mL), EtOH (18 mL), and 1.00N NaOHaq (5 mL, 0.005 mole) was placed in a conical flask and stirred vigorously (magnetic stirrer) for 40 minutes to give a pale yellow solution. This solution was kept at 22° C. for 18.5 hours. It was then filtered through a bed of Celite (carbon treatment) and the clear filtrate acidified to pH 2.5 with 1.00 N HClaq. The resulting white gelatinous precipitate of the product was centrifuged (1500g/30 minutes) and washed by three cycles of resuspension (H2 0: 80 mL, 80 mL, and 40 mL)--centrifugation--decantation. The pellet was dried in vacuo over P2 05 --first at 22° C./24 hours in a desiccator and then at 80° C./4 hours in a pistol. A pale yellow amorphous solid was obtained (0.312 g, 67.5%),

Workup

  1. customwas placed in a conical flask
  2. customto give a pale yellow solution
  3. waitThis solution was kept at 22° C. for 18.5 hours
  4. filtrationIt was then filtered through a bed of Celite (carbon treatment)
  5. custom(1500g/30 minutes)
  6. washwashed by three cycles of resuspension (H2 0: 80 mL, 80 mL, and 40 mL)
  7. customThe pellet was dried in vacuo over P2 05
  8. customat 22° C.
  9. custom24 hours
  10. customat 80° C.
  11. custom4 hours
  12. customA pale yellow amorphous solid was obtained (0.312 g, 67.5%)

Sources & evidence

ORD record
ord-51511cdcb2cb439db0b04c1b6cfe5f3c
Source dataset
uspto-grants-1993_08
Patent number
US05236927

Reaction notes

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