Trifluoroacetic acid → HCID 71060411, compound

HRID 1036713Notes

Reaction equation

HRID 1036713 reaction equation
C(OC([N:8]1[CH2:25][CH2:24][CH2:23][C:10]2([C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][N:12]([CH3:21])[C:11]2=[O:22])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:21][N:12]1[N:13]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]2([CH2:23][CH2:24][CH2:25][NH:8][CH2:9]2)[C:11]1=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060352HCID 71060352, compound

Product 1

HCID 71060411HCID 71060411, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of a racemic mixture of 3-Methyl-4-oxo-1-phenyl-2,3,7-triaza-spiro[4.5]dec-1-ene-7-carboxylic acid tert-butyl ester (110 mg, 0.32 mmol) in DCM (5 ml) was added TFA (0.5 ml). The reaction mixture was stirred at RT for 1 hour. The reaction mixture was applied to a 1 g SCX-2 cartridge. The impurities were eluted with 1:1 DCM:MeOH, followed by 0.05M ammonia in 1:1 DCM:MeOH. The product was eluted with 1M ammonia in 1:1 DCM:MeOH and the clean fractions were concentrated in vacuo to afford the title compound. No further purification was performed on the title compound.

Workup

  1. washThe impurities were eluted with 1:1 DCM
  2. washThe product was eluted with 1M ammonia in 1:1 DCM
  3. concentrationMeOH and the clean fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-30433e8ef3404144aeb065cac8aca864
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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