Trifluoromethanesulfonic anhydride → HCID 70169699, compound

HRID 2306266Notes

Reaction equation

HRID 2306266 reaction equation
[CH:1]([Si:4]([O:11][C:12](=[O:52])[N:13]([C@H:40]1[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41]1)[CH2:14][CH2:15][C:16]1[N:17]=[CH:18][N:19](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:20]=1)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[C:53]([C:55]1[CH:62]=[CH:61][C:58]([CH2:59]O)=[CH:57][C:56]=1[F:63])#[N:54].C(N(CC)C(C)C)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>C(Cl)Cl>[CH:1]([Si:4]([O:11][C:12](=[O:52])[N:13]([C@H:40]1[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])[CH2:41]1)[CH2:14][CH2:15][C:16]1[N:17]([CH2:59][C:58]2[CH:61]=[CH:62][C:55]([C:53]#[N:54])=[C:56]([F:63])[CH:57]=2)[CH:18]=[N:19][CH:20]=1)([CH:5]([CH3:6])[CH3:7])[CH:8]([CH3:10])[CH3:9])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrileHCID 70171841HCID 70171841, compound

Product 1

HCID 70169699HCID 70169699, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-N-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]-N-{2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}carbamic acid triisopropylsilyl ester, as described above in Step F, (519 mg, 0.715 mmol) and 4-cyano-3-fluoro-benzyl alcohol, as described in Example 31, Step H, (108 mg, 0.715 mmol) in CH2Cl2 (7 mL) was added N,N-diisopropylethylamine (0.311 mL, 1.78 mmol), followed by dropwise addition of trifluoromethanesulfonic anhydride (0.120 mL, 0.715 mmol). The reaction mixture was allowed to warm slowly to ambient temperature and was stirred for 18 hours, then concentrated in vacuo. The residue was dissolved in MeOH (10 mL) and the resulting solution was heated to 40° C. for 2 hours. The solvent was removed in vacuo and the residue was chromatographed on silica gel, eluting with a gradient of CH2Cl2—1% to 4% MeOH—0.1% to 0.4% NH4OH, to yield the above-titled compound.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH (10 mL)
  3. temperaturethe resulting solution was heated to 40° C. for 2 hours
  4. customThe solvent was removed in vacuo
  5. customthe residue was chromatographed on silica gel
  6. washeluting with a gradient of CH2Cl2—1% to 4% MeOH—0.1% to 0.4% NH4OH

Sources & evidence

ORD record
ord-377de62064f24f54b15cda29af8d976a
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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