Sodium Bicarbonate → HCID 69709981, compound

HRID 2121897Notes

Reaction equation

HRID 2121897 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][O:8][C@H:9]1[CH2:32][O:31][C:12]2=[CH:13][CH:14]=[C:15]3[C:19]([N:18]([CH2:20][C@H:21]([O:23][Si](C(C)(C)C)(C)C)[CH3:22])[N:17]=[CH:16]3)=[C:11]2[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:33])[CH2:7][O:8][C@H:9]1[CH2:32][O:31][C:12]2=[CH:13][CH:14]=[C:15]3[C:19]([N:18]([CH2:20][C@H:21]([OH:23])[CH3:22])[N:17]=[CH:16]3)=[C:11]2[CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 69884487HCID 69884487, compound

Product 1

HCID 69709981HCID 69709981, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from step A (2.60 g, 4.41 mmol) and a solution of tetrabutylammonium fluoride (1 M, 1.52 mmol) in THF (3 mL) was stirred at ambient temperature overnight, mixed with a saturated aqueous solution of sodium bicarbonate (50 mL) and extracted with ethyl acetate. The extract was purified by chromatography (silica, gradient 10% to 40% ethyl acetate in hexane) to give an oil (1.32 g, 82%): LCMS (+APCI) m/z 363 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe extract was purified by chromatography (silica, gradient 10% to 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-691b4689b6bc470a847ec2a31016e60f
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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