Sodium Bicarbonate → HCID 9969649, compound

HRID 1263534Notes

Reaction equation

HRID 1263534 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[CH:23]1[CH2:28][CH2:27][C:26](=[N:29][NH:30][S:31]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[CH2:25][CH2:24]1)(C(C)(C)C)(C)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>C(O)(=O)C.O1CCCC1>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[CH:23]1[CH2:24][CH2:25][C:26](=[N:29][NH:30][S:31]([C:34]2[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=2)(=[O:33])=[O:32])[CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 69901544HCID 69901544, compound

Product 1

HCID 9969649HCID 9969649, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a round bottomed flask was added N′-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylidene-4-methylbenzenesulfonohydrazide (100 mg), tetrahydrofuran (5 ml), glacial acetic acid (3 drops) and tetrabutylammonium fluoride hydrate (174 mg), and the resulting solution was stirred at room temperature for 2 hr. Saturated sodium hydrogen carbonate solution (10 ml) was added and stirring was continued for 1 hr. The reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml), the layers were separated, and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic phases were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 7:3 v/v) furnished the title compound (62 mg, 100%) as a cream solid. δH ((CD3)2CO): 1.44-1.63 (2H, m), 1.92-2.01 (3H, m), 2.22-2.32 (1H, m), 2.35-2.43 (2H, m), 2.97 (3H, s), 3.09 (1 H, tt), 6.28 (1 H, dd), 6.37 (1 H, d), 6.87 (1 H, d), 7.38 (2H, d), 7.79 (2H, d), 7.96 (1H, s), 8.13 (1H, s), 8.99 (1H, s); m/z (ES+) 375 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hr
  3. customThe reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml)
  4. customthe layers were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (2×20 ml)
  6. washThe combined organic phases were washed with brine (10 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 7:3 v/v)

Sources & evidence

ORD record
ord-18175b74ac71400ebb8a2ab3fd2e1e2a
Source dataset
uspto-grants-2003_04
Patent number
US06541473B2

Reaction notes

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