Sodium Bicarbonate → HCID 22083004, compound

HRID 2187884Notes

Reaction equation

HRID 2187884 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:41])[C:10]([NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=2)[CH:16]=[CH:15][CH:14]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:41])[C:10]([NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([OH:23])[CH:21]=2)[CH:16]=[CH:15][CH:14]=1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 70149057HCID 70149057, compound

Product 1

HCID 22083004HCID 22083004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-2-(tert-butoxycarbonylamino)-N-[7-(tert-butyldiphenylsilyloxy)naphthalen-1-yl]propionamide (290 mg, 0.51 mmol) in dry THF (2 mL), under argon, was added TBAF (0.56 mL of a 1.0 M solution in THF, 0.56 mmol) dropwise. The resulting mixture was stirred at ambient temperature for 30 min, then saturated aqueous NaHCO3 (1 mL) was added and the THF was removed under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 (10 mL) and CH2Cl2 (30 mL). The aqueous layer was extracted further with CH2Cl2 (30 mL) and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with a gradient of CH2Cl2-10% to 30% EtOAc to yield the titled product as a pale solid.

Workup

  1. customthe THF was removed under reduced pressure
  2. customThe residue was partitioned between saturated aqueous NaHCO3 (10 mL) and CH2Cl2 (30 mL)
  3. extractionThe aqueous layer was extracted further with CH2Cl2 (30 mL)
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography on silica
  8. washeluting with a gradient of CH2Cl2-10% to 30% EtOAc

Sources & evidence

ORD record
ord-75a837846a2e49a1bc0501b205bf98c9
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

Loading…