Trifluoroacetic acid → HCID 59238164, compound

HRID 2068569Notes

Reaction equation

HRID 2068569 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[CH:19][N:18]([CH:24]([C:31]([O:33]C(C)(C)C)=[O:32])[CH2:25][O:26]C(C)(C)C)[C:17]3=[O:38])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[OH:26][CH2:25][CH:24]([N:18]1[C:17](=[O:38])[C:16]2[C:21](=[CH:22][CH:23]=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:15]=2)[N:20]=[CH:19]1)[C:31]([OH:33])=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59238179HCID 59238179, compound

Product 1

HCID 59238164HCID 59238164, compoundYield 156.1%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

4-[3-(2-tert-butoxy-1-tert-butoxycarbonyl-ethyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-piperazine-1-carboxylic acid tert-butyl ester (4.7 g) was dissolved in anisole (8 mL) and cooled in an ice-water bath. Trifluoroacetic acid (80 mL) is added slowly. The mixture was stirred for 5 minutes while cooling with the ice-water bath and then for 5 hours at room temperature; during this time, the color of the reaction mixture changed from orange to red to purple to dark blue over time. At this time, the reaction solvents were removed in vacuo, leaving a blue oil. This oil was triturated with dry diethyl ether and evaporated to dryness again. The residue was again triturated with dry diethyl ether and stirred overnight with this solvent. At this time, the mixture was filtered and the resulting solid was washed with diethyl ether and dried in a vacuum oven, resulting in 4.4 g of a solid. This solid was used in the next step without further purification. H1-NMR spectroscopy indicated a spectrum consistent with 3-hydroxy-2-(4-oxo-6-piperazin-1-yl-4H-quinazolin-3-yl)-propionic acid.

Workup

  1. temperaturecooled in an ice-water bath
  2. waitfor 5 hours at room temperature
  3. customAt this time, the reaction solvents were removed in vacuo
  4. customleaving a blue oil
  5. customThis oil was triturated with dry diethyl ether
  6. customevaporated to dryness again
  7. customThe residue was again triturated with dry diethyl ether
  8. stirringstirred overnight with this solvent
  9. filtrationAt this time, the mixture was filtered
  10. washthe resulting solid was washed with diethyl ether
  11. customdried in a vacuum oven

Sources & evidence

ORD record
ord-3b804325b4ca42f98afbf72085aea473
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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