Sodium Bicarbonate → HCID 69709561, compound

HRID 2121903Notes

Reaction equation

HRID 2121903 reaction equation
C([Si](C)(C)[O:6][C@H:7]([CH3:29])[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]3[O:21][CH2:20][C@H:19]([O:22][CH2:23][CH2:24][NH:25][C:26](=[O:28])[CH3:27])[CH2:18][C:16]3=2)[CH:11]=[N:10]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>C1COCC1>[OH:6][C@H:7]([CH3:29])[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]3[O:21][CH2:20][C@H:19]([O:22][CH2:23][CH2:24][NH:25][C:26](=[O:28])[CH3:27])[CH2:18][C:16]3=2)[CH:11]=[N:10]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 69710047HCID 69710047, compound

Product 1

HCID 69709561HCID 69709561, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from Step C (0.41 g, 0.92 mmol) and tetrabutylammonium fluoride (1 M, 1.84 mL, 1.84 mmol) in THF (30 mL) was stirred at ambient temperature for 4 h, mixed with a saturated aqueous solution of sodium bicarbonate (50 mL) and extracted with ethyl acetate. The dried extracts were evaporated to a residue which was purified by chromatography (silica, gradient, ethyl acetate to 10% methanol in ethyl acetate) a colorless solid (0.23 g, 75%): mp 165-166° C. LCMS (+ESI) m/z 334 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe dried extracts were evaporated to a residue which
  3. customwas purified by chromatography (silica, gradient, ethyl acetate to 10% methanol in ethyl acetate) a colorless solid (0.23 g, 75%)

Sources & evidence

ORD record
ord-482980e2eeb24f148363cd1aa3971830
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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