Sodium Bicarbonate → HCID 178474955, compound

HRID 2307159Notes

Reaction equation

HRID 2307159 reaction equation
[Si]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si](C(C)(C)C)(C)C)[CH:12]=[CH:11][C:10]=1[C@H:23]1[CH2:28][CH2:27][C@H:26]([NH:29][C:30](=[O:32])[CH3:31])[CH2:25][CH2:24]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[C@H:23]1[CH2:24][CH2:25][C@H:26]([NH:29][C:30](=[O:32])[CH3:31])[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium Fluoride2×HCID 178474957HCID 178474957, compound

Product 1

HCID 178474955HCID 178474955, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a round bottomed flask equipped with magnetic stirrer was added cis/trans-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl] acetamide (15 mg, 31 μmol), tetrahydrofuran (3 ml) and tetra-n-butylammonium fluoride (93 μl, 93 μmol, 1.0M solution in tetrahydrofuran). The resulting solution was stirred for 3 hr. Tetra-n-butylammonium fluoride (90 μl, 90 μmol, 1.0M solution in tetrahydrofuran) was added and the solution stirred for a further 64 hr. Saturated aqueous sodium bicarbonate solution (3 ml) was added and the solvents removed in vacuo. The residue was partitioned between ethyl acetate (20 ml) and water (5 ml) and the aqueous layer extracted with ethyl acetate (3×10 ml). The combined organic layers were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash column chromatography (SiO2, methanol/dichloromethane, 1:9, v/v) afforded an oily solid (6 mg) which was a mixture of isomers by NMR. Further purification via HPLC afforded the title compound (0.5 mg, 6%) as a mixture of diastereoisomers and a colourless oil. m/z (ES−) 308 (M−1+60{acetate}); δH(CD3OD) 1.41 (1H, m), 1.57 (1H, m), 1.70 (2H, m), 1.83 (1H, m), 1.87 (1H, m), 1.93 (1H, m), 1.96 (1.5H, m), 2.04 (1.5H, m), 2.05 (1H, m), 2.82 (1H, m), 3.72 (0.5H, m), 4.14 (0.5H, m), 6.28 (2H, m), 6.92 (0.5H, dd), 6.97 (0.5H, dd).

Workup

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. stirringthe solution stirred for a further 64 hr
  3. customthe solvents removed in vacuo
  4. customThe residue was partitioned between ethyl acetate (20 ml) and water (5 ml)
  5. extractionthe aqueous layer extracted with ethyl acetate (3×10 ml)
  6. washThe combined organic layers were washed with brine (10 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification via flash column chromatography (SiO2, methanol/dichloromethane, 1:9, v/v)

Sources & evidence

ORD record
ord-b5e9bce369cc401aa1fd277b753e6441
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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