Diethyl Pyrocarbonate → HCID 18919289, compound

HRID 1291360Notes

Reaction equation

HRID 1291360 reaction equation
[C:1]([C:4]1[CH:32]=[CH:31][C:7]([C:8]([C:10]2[CH:30]=[CH:29][C:13]([CH2:14][S:15][C:16]3[N:25]([CH3:26])[C:24](=[O:27])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][C:22]=4[CH3:28])[N:17]=3)=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.CCOC(OC(OCC)=O)=O.[OH:44][CH:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>CN(C=O)C>[CH3:26][N:25]1[C:24](=[O:27])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH3:28])[N:17]=[C:16]1[S:15][CH2:14][C:13]1[CH:12]=[CH:11][C:10]([C:8](=[O:9])[C:7]2[CH:6]=[CH:5][C:4]([C:1]([N:48]3[CH2:49][CH2:50][CH:45]([OH:44])[CH2:46][CH2:47]3)=[O:3])=[CH:32][CH:31]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 79341Piperidin-4-olHCID 18918934HCID 18918934, compound

Product 1

HCID 18919289HCID 18919289, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(4-carboxybenzoyl)benzyl]thio-3,5-dimethyl-4(3H)-quinazolinone (1.00 g, 2.26 mmol) in DMF (10.0 ml) was added DEPC (0.755 g, 4.63 mmol) and the mixture was stirred at room temperature for 10 minutes. Then, 4-hydroxypiperidine (0.522 g, 5.16 mmol) was added and the mixture was stirred at room temperature for 4 hours. The solvent was then distilled off and the residue was dissolved in ethyl acetate and washed with saturated aqueous NaCl solution. The organic layer was dried over MgSO4 and then concentrated under reduced pressure, and the residue was recrystallized from THF to provide colorless needles.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. distillationThe solvent was then distilled off
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous NaCl solution
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was recrystallized from THF
  8. customto provide colorless needles

Sources & evidence

ORD record
ord-ad8430344d0542759610da65048c6a05
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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