Dimethyl Sulfate → HCID 15341827, compound

HRID 893468Notes

Reaction equation

HRID 893468 reaction equation
[OH:1][C:2]1[C:3]([CH2:36][CH2:37][CH3:38])=[C:4]([CH:26]=[CH:27][C:28]=1[C:29]([N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:30])[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([CH2:23][CH2:24][CH3:25])=[C:12]([CH:20]=[CH:21][CH:22]=1)[O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH2:39]1COCC1.[OH-].[K+].S(OC)(OC)(=O)=O>C(OCC)(=O)C.CCCCCC.O>[CH3:39][O:1][C:2]1[C:3]([CH2:36][CH2:37][CH3:38])=[C:4]([CH:26]=[CH:27][C:28]=1[C:29]([N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:30])[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([CH2:23][CH2:24][CH3:25])=[C:12]([CH:20]=[CH:21][CH:22]=1)[O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 15341826HCID 15341826, compound

Product 1

HCID 15341827HCID 15341827, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound of Example 48 (200 mg, 0.3789 mmol) was added to 2.0 ml of THF then potassium hydroxide (25.5 mg, 0.4546 mmol) was added followed by dimethyl sulfate (71.7 mg, 0.5683 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water and extracted three times with ethyl acetate and the combined extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed under vacuum to give an oil. Chromatography of the oil on silica gel with 50/50 ethyl acetate/hexane as eluant gave the product.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialthe combined extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed under vacuum
  5. customto give an oil

Sources & evidence

ORD record
ord-768fe48ef6454ca4be3962420eaf287a
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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