Trifluoroacetic acid → HCID 178525169, compound

HRID 1027141Notes

Reaction equation

HRID 1027141 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:15]2([CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[O:14][CH2:13][C@H:12]1[C:21]1[NH:22][CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][C:35]([C:38]4[N:39]=[C:40]([C@@H:43]5[CH2:47][CH2:46][CH2:45][N:44]5C(OC(C)(C)C)=O)[NH:41][CH:42]=4)=[CH:34][CH:33]=3)=[CH:28][CH:27]=2)[N:25]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[C:15]2([CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[O:14][CH2:13][C@H:12]1[C:21]1[NH:22][CH:23]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][C:35]([C:38]4[N:39]=[C:40]([C@@H:43]5[CH2:47][CH2:46][CH2:45][NH:44]5)[NH:41][CH:42]=4)=[CH:34][CH:33]=3)=[CH:28][CH:27]=2)[N:25]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451918HCID 178451918, compound

Product 1

HCID 178525169HCID 178525169, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-3-(4-{4′-[2-((S)-1-tert-Butoxycarbonyl-pyrrolidin-2-yl)-1H-imidazol-4-yl]-biphenyl-4-yl}-1H-imidazol-2-yl)-1,8-dioxa-4-aza-spiro[4.5]decane-4-carboxylic acid benzyl ester (0.04 gm, 0.05 mmol) was dissolved in DCM (2 mL), TFA (2 mL) was added and the mixture stirred for 2 hours. The solvent was evaporated, the residue redissolved in EtOAc (20 mL) and the organics washed with aqueous NaHCO3, water and brine. Drying the organic layer afforded (R)-3-{4-[4′-((S)-2-pyrrolidin-2-yl-1H-imidazol-4-yl)-biphenyl-4-yl]-1H-imidazol-2-yl}-1,8-dioxa-4-aza-spiro[4.5]decane-4-carboxylic acid benzyl ester (0.015 gm, 44%). LCMS 631.0 (M+1).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue redissolved in EtOAc (20 mL)
  3. washthe organics washed with aqueous NaHCO3, water and brine
  4. customDrying the organic layer

Sources & evidence

ORD record
ord-8c5802efdb4a401aa5db689043241188
Source dataset
uspto-grants-2014_05
Patent number
US08729077B2

Reaction notes

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