Water → HCID 70300110, compound

HRID 1106912Notes

Reaction equation

HRID 1106912 reaction equation
[C:1]([O:5][C:6](=[O:45])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([N:30]([C:32](=[O:44])[CH2:33][C:34]2[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=2)[CH3:31])[CH2:16][CH:17]2[CH2:21][CH2:20][CH:19]([O:22][Si](C(C)(C)C)(C)C)[CH2:18]2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:45])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([N:30]([C:32](=[O:44])[CH2:33][C:34]2[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=2)[CH3:31])[CH2:16][CH:17]2[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 70298375HCID 70298375, compound

Product 1

HCID 70300110HCID 70300110, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of Example 41 (1.23 g, 1.86 mmol) in tetrahydrofuran (3 mL) was added tetrabutylammonium fluoride (1.0 M in tetrahydrofuran) (1.9 mL, 1.9 mmol). The reaction was stirred at room temperature under argon for 4 hours, then the reaction was poured into water (20 mL). Brine (80 mL) was added, and the reaction extracted with dichloromethane (3×80 mL). The organics were dried (MgSO4) and the solvent removed in vacuo. Column chromatography (dichloromethane:methanol 9:1) gave the product as a white foam, 1.54 mmol, 83%.

Workup

  1. extractionthe reaction extracted with dichloromethane (3×80 mL)
  2. dry with materialThe organics were dried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-751bb9e663de4f548643f065056ff4e9
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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