Trifluoroacetic acid → HCID 58393217, compound

HRID 469075Notes

Reaction equation

HRID 469075 reaction equation
[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([N:26]3[CH2:34][CH:33]4[CH:28]([CH2:29][N:30](C(OC(C)(C)C)=O)[CH2:31][CH2:32]4)[CH2:27]3)=[O:25])[N:23]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([N:26]3[CH2:34][CH:33]4[CH:28]([CH2:29][NH:30][CH2:31][CH2:32]4)[CH2:27]3)=[O:25])[N:23]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58393216HCID 58393216, compound

Product 1

HCID 58393217HCID 58393217, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to general procedure AN using tert-butyl 2-{[2-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazol-4-yl]carbonyl}octahydro-5H-pyrrolo[3,4-c]pyridine-5-carboxylate (245 mg, 0.42 mmol), TFA (1 mL) and DCM (3 mL). Following the completion of the reaction the solvent was removed in vacuo, the residue redissolved in DCM (2 mL), absorbed on to 2 g SCX cartridge and washed with DCM (5 mL) and MeOH (5 mL). The title compound was eluted with 7 N NH3 in MeOH (10 mL) and concentrated in vacuo.

Workup

  1. customthe completion of the reaction the solvent
  2. customwas removed in vacuo
  3. dissolutionthe residue redissolved in DCM (2 mL)
  4. customabsorbed on to 2 g SCX cartridge
  5. washwashed with DCM (5 mL) and MeOH (5 mL)
  6. washThe title compound was eluted with 7 N NH3 in MeOH (10 mL)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a919778334746de9ebf062b1a7fae1d
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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