Sodium t-butoxide → HCID 74788457, compound

HRID 406790Notes

Reaction equation

HRID 406790 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 rt 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, 2 H), 6.48-6.44 (m, 2 H), 5.48 (bs, 1H), 3.94-3.90 (m, 1 H), 3.70-3.65 (m, 2 H), 2.64-2.60 (m, 1 H), 1.84-1.81 (m, 1 H), 1.45-1.39 (m, 10 H), 0.98-0.95 (m, 2 H), 0.76-0.73 (m, 1 H), 6.64-6.62 (m, 2 H), 0.35-0.34 (m, 2 H).

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-66bb232d1d6b4867a7e4586f19ef8007
Source dataset
uspto-grants-2014_06
Patent number
US08754132B2

Reaction notes

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