Trifluoroacetic acid → HCID 23627628, compound

HRID 1423114Notes

Reaction equation

HRID 1423114 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[CH2:28][C:29]1[N:30]=[CH:31][N:32](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[CH2:28][C:29]1[NH:30][CH:31]=[N:32][CH:33]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66826183HCID 66826183, compound

Product 1

HCID 23627628HCID 23627628, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The intermediate (S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-1-(1-trityl-1H-imidazol-4-ylmethyl)-piperazine (90 mg, 0.13 mmol) was dissolved in CH2Cl2 (0.5 mL) and was treated with triethylsilane (0.5 mL) followed by trifluoroacetic acid (1.0 mL). The reaction mixture was stirred for 2 h then evaporated to a residue which was triturated with a 10% EtOAc/hexane solution (4×1 mL). The residue was then partitioned between EtOAc (1 mL) and a saturated aqueous K2CO3 solution (0.5 mL). The organic component was separated, dried over MgSO4, filtered, and evaporated to afford the title compound as a foam (50 mg, 83%). LC/MS (Method A) 4.50 min, [M+1]+ 447.

Workup

  1. customthen evaporated to a residue which
  2. customwas triturated with a 10% EtOAc/hexane solution (4×1 mL)
  3. customThe residue was then partitioned between EtOAc (1 mL)
  4. customThe organic component was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cbababb0a1934dfeb47a57d5d291abee
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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