Trifluoroacetic acid → {2,4-dioxo-3-[4-(phenethylcarbamoyl-methyl)-phenyl]-3,4-dihydro-2H-quinazolin-1-yl}-acetic acid

HRID 472745Notes

Reaction equation

HRID 472745 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C:26](=[O:36])[NH:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:21][CH:20]=2)[C:9]1=[O:37])(C)(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:37]=[C:9]1[N:10]([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C:26](=[O:36])[NH:27][CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:23][CH:24]=2)[C:11](=[O:18])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]1[CH2:7][C:6]([OH:38])=[O:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68593254{2,4-dioxo-3-[4-(phenethylcarbamoyl-methyl)-phenyl]-3,4-dihydro-2H-quinazolin-1-yl}-acetic acid tert-butyl ester2×

Product 1

HCID 68588311{2,4-dioxo-3-[4-(phenethylcarbamoyl-methyl)-phenyl]-3,4-dihydro-2H-quinazolin-1-yl}-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of {2,4-dioxo-3-[4-(phenethylcarbamoyl-methyl)-phenyl]-3,4-dihydro-2H-quinazolin-1-yl}-acetic acid tert-butyl ester (Intermediate E) (470 mg, 0.916 mmol) and triethylsilane (0.37 ml, 2.9 mmol) in dry DCM (2.5 ml) under argon is treated dropwise with TFA (2.5 ml). After 18 hours, the reaction mixture is evaporated in vacuo and the residue is triturated with MeOH resulting in a white solid. The solid is filtered and dried under vacuum to afford the title compound.

Workup

  1. customthe reaction mixture is evaporated in vacuo
  2. customthe residue is triturated with MeOH resulting in a white solid
  3. filtrationThe solid is filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-eb69a9541bbd42c2bf6e3c131ef8819d
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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