Sodium Bicarbonate → HCID 20081848, compound

HRID 1609572Notes

Reaction equation

HRID 1609572 reaction equation
C([CH:5]([O:28][SiH](C)C)[C:6]1[C:7]([CH:25]2[CH2:27][CH2:26]2)=[N:8][C:9]([CH:22]([CH3:24])[CH3:23])=[C:10]([CH2:19][O:20][CH3:21])[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>O1CCCC1>[CH:25]1([C:7]2[C:6]([CH2:5][OH:28])=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:10]([CH2:19][O:20][CH3:21])=[C:9]([CH:22]([CH3:24])[CH3:23])[N:8]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 137329062HCID 137329062, compound

Product 1

HCID 20081848HCID 20081848, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.7 g (12.8 mmol) of the crude product from Example 148 are dissolved in absolute tetrahydrofuran. After addition of 12.8 ml of tetrabutylammonium fluoride solution (1M in THF) the mixture is stirred overnight at room temperature. 50 ml of saturated sodium hydrogen carbonate solution are then added and the mixture is extracted several times with methylene chloride. The combined organic phases are dried with sodium sulphate, concentrated and chromatographed over silica gel (eluent: petroleum ether/ethyl acetate 713).

Workup

  1. extractionthe mixture is extracted several times with methylene chloride
  2. dry with materialThe combined organic phases are dried with sodium sulphate
  3. concentrationconcentrated
  4. customchromatographed over silica gel (eluent: petroleum ether/ethyl acetate 713)

Sources & evidence

ORD record
ord-1b63c6bf689c41c4bde9d74651b313fc
Source dataset
uspto-grants-1995_03
Patent number
US05401746

Reaction notes

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