Dimethyl Sulfate → HCID 15341839, compound

HRID 893476Notes

Reaction equation

HRID 893476 reaction equation
[CH:1]1([CH2:4][C:5]2[C:35]([OH:36])=[C:34]([C:37]([NH:39][CH3:40])=[O:38])[CH:33]=[CH:32][C:6]=2[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:28]=[CH:27][C:15]3[CH2:16][CH2:17][CH:18]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:19][C:14]=3[C:13]=2[CH2:29][CH2:30][CH3:31])[CH2:3][CH2:2]1.[CH2:41]1COCC1.[OH-].[K+].S(OC)(OC)(=O)=O>C(OCC)(=O)C.CCCCCC.O>[CH:1]1([CH2:4][C:5]2[C:35]([O:36][CH3:41])=[C:34]([C:37]([NH:39][CH3:40])=[O:38])[CH:33]=[CH:32][C:6]=2[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:28]=[CH:27][C:15]3[CH2:16][CH2:17][CH:18]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:19][C:14]=3[C:13]=2[CH2:29][CH2:30][CH3:31])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 15341838HCID 15341838, compound

Product 1

HCID 15341839HCID 15341839, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound of Example 60 (I70 mg, 0.31 mmol) was added to about 5.0 ml of THF. Potassium hydroxide (21.2 mg, 0.38 mmol) was added and the mixture was stirred for 10 min. Dimethyl sulfate (59.6 mg, 0.47 mmol) was added, and the reaction mixture was stirred for 4 hours at room temperature. Water (10 ml) was added to the reaction mixture, and it was extracted three times with ethyl acetate. The combined extracts were filtered, and the solvent was removed under vacuum to give an oil. Chromatography of the oil on silica gel with 40/60 ethyl acetate/hexane gave the product as a colorless oil (160 mg).

Workup

  1. stirringthe reaction mixture was stirred for 4 hours at room temperature
  2. extractionwas extracted three times with ethyl acetate
  3. filtrationThe combined extracts were filtered
  4. customthe solvent was removed under vacuum
  5. customto give an oil

Sources & evidence

ORD record
ord-17ac9fae87a048828e8bfa9291b26199
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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