Trifluoroacetic acid → HCID 16124454, compound

HRID 1690131Notes

Reaction equation

HRID 1690131 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:20][CH2:19][C@:18]3([CH2:24][CH2:23][NH:22][C:21]3=[O:25])[N:17]2C(OC(C)(C)C)=O)=[CH:12][CH:11]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C@H:16]2[CH2:20][CH2:19][C@:18]3([CH2:24][CH2:23][NH:22][C:21]3=[O:25])[NH:17]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58027442HCID 58027442, compound

Product 1

HCID 16124454HCID 16124454, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl (2R,5R)-2-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (D26, 30 mg) was dissolved in dry DCM (1.5 ml). At 0° C. TFA (0.4 ml) was added and the mixture was stirred at room temperature for 1 h. The mixture was evaporated and the residue purified via a SCX cartridge affording the title compound (23 mg) as a yellowish oil. Rt (HPLC) 3.61 min; MS: (ES/+) m/z: 341 [MH+]. C20H21FN2O2 requires 340.

Workup

  1. customAt 0° C
  2. customThe mixture was evaporated
  3. customthe residue purified via a SCX cartridge

Sources & evidence

ORD record
ord-85a6c830998e413192e4ff8f88048b55
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

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