Sodium t-butoxide → HCID 74788457, compound

HRID 453944Notes

Reaction equation

HRID 453944 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][C@@H:9]1[CH2:11][C@H:10]1[C:12]1[CH:17]=[C:16]([O:18]C(=O)C(C)(C)C)[CH:15]=[CH:14][C:13]=1[O:25][CH2:26][CH:27]1[CH2:29][CH2:28]1)([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[Na+]>CO>[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][C@@H:9]1[CH2:11][C@H:10]1[C:12]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:13]=1[O:25][CH2:26][CH:27]1[CH2:29][CH2:28]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 23676156Sodium t-butoxideHCID 74788459HCID 74788459, compound

Product 1

HCID 74788457HCID 74788457, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 16 (127 mg, 0.304 mmol) in MeOH (1 mL) was treated with NaOtBu (146 mg, 1.52 mmol) at 0° C. After stirring at it for 4 h, the reaction was quenched adding sat. NH4Cl (2 mL) and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using gradient elution from 0% EtOAc-hexane to 30% EtOAc-hexane to afford the title compound as a thick oil (95 mg, 94% yield). 1H NMR (400 MHz, CDCl3) δ 6.68-6.60 (m, 2H), 6.48-6.44 (m, 2H), 5.48 (bs, 1H), 3.94-3.90 (m, 1H), 3.70-3.65 (m, 2H), 2.64-2.60 (m, 1H), 1.84-1.81 (m, 1H), 1.45-1.39 (m, 10H), 0.98-0.95 (m, 2H), 0.76-0.73 (m, 1H), 6.64-6.62 (m, 2H), 0.35-0.34 (m, 2H).

Workup

  1. customthe reaction was quenched
  2. additionadding sat. NH4Cl (2 mL)
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography
  9. washelution from 0% EtOAc-hexane to 30% EtOAc-hexane

Sources & evidence

ORD record
ord-b2ac49811d4546e0acc1ee08b6b9c498
Source dataset
uspto-grants-2013_07
Patent number
US08492591B2

Reaction notes

Loading…