Sodium Bicarbonate → HCID 70171511, compound

HRID 2306276Notes

Reaction equation

HRID 2306276 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][Si](C(C)(C)C)(C)C)=[CH:7][CH:8]=2)[C:3]=1[N:20]1[CH2:24][CH2:23][C@H:22]([NH:25][C:26](=[O:43])[CH2:27][C:28]2[N:32]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[C:36]([F:42])[CH:35]=3)[CH:31]=[N:30][CH:29]=2)[C:21]1=[O:44].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[C:3]=1[N:20]1[CH2:24][CH2:23][C@H:22]([NH:25][C:26](=[O:43])[CH2:27][C:28]2[N:32]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[C:36]([F:42])[CH:35]=3)[CH:31]=[N:30][CH:29]=2)[C:21]1=[O:44]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 70171744HCID 70171744, compound

Product 1

HCID 70171511HCID 70171511, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-N-{1-[2-Bromo-7-(tert-butyldimethylsilyloxy)naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-2-[1-(4-cyano-3-fluorobenzyl)-1H-imidazol-5-yl]acetamide, as described above in Step K, (171 mg, 0.264 mmol) was dissolved in THF (5 mL) and TBAF (1.0 M in THF, 0.26 mL, 0.26 mmol) was added. After 45 min, the mixture was poured into saturated aqueous NaHCO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with a gradient of CH2Cl2—1% to 10% MeOH—0.1% to 1% NH4OH, to yield the above-titled compound.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washeluting with a gradient of CH2Cl2—1% to 10% MeOH—0.1% to 1% NH4OH

Sources & evidence

ORD record
ord-15c6d9e2d3ba411b9be5a1cffa9ab0fc
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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