Sodium Chloride → HCID 69712204, compound

HRID 2121907Notes

Reaction equation

HRID 2121907 reaction equation
[Si]([O:8][C@H:9]([CH3:29])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]3[O:23][CH2:22][C@H:21]([O:24][CH2:25][C:26]([NH2:28])=[O:27])[CH2:20][C:18]3=2)[CH:13]=[N:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C1COCC1>[OH:8][C@H:9]([CH3:29])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]3[O:23][CH2:22][C@H:21]([O:24][CH2:25][C:26]([NH2:28])=[O:27])[CH2:20][C:18]3=2)[CH:13]=[N:12]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 69885696HCID 69885696, compound

Product 1

HCID 69712204HCID 69712204, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Step B (0.44 g, 1.05 mol) was dissolved in THF (20 mL) and a solution of tetrabutylammonium fluoride in THF (1 M, 2.1 mL, 2.1 mmol) was added; this mixture was stirred for 2 h at room temperature. A saturated aqueous solution of sodium bicarbonate (100 mL) was added and the mixture was saturated with sodium chloride and extracted with ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4) and evaporated to give a yellow oil (0.47 g) which was purified by chromatography (silica gel, gradient, ethyl acetate; 5% methanol in ethyl acetate; 10% methanol in ethyl acetate) to give a colorless oil (0.30 g, 94%): LC/MS (+APCI) m/z 306.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-24ae2341973c4330bce7ed41a3b6d8bc
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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