Dimethyl Sulfate → HCID 73074217, compound

HRID 455003Notes

Reaction equation

HRID 455003 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:22])[CH:9]1[CH:13]([OH:14])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][Si]([N-][Si](C)(C)C)(C)C.[K+].S(OC)(OC)(=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH3:22])[CH:9]1[CH:13]([O:14][CH3:23])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 67309978HCID 67309978, compound

Product 1

HCID 73074217HCID 73074217, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 6 (9.9 kg) was treated with a solution of KHMDS (35 kg, 20% w/w) in THF, followed by dimethyl sulfate (4.7 kg). After completion of the reaction, the reaction mixture was quenched with 5% acetic acid in water. The product was extracted with MTBE, and the organic layer concentrated to give crude product (7). This was treated with p-toluene sulfonic acid monohydrate (TsOH) in a tetrahydrofuran-methanol mixture. After completion of the reaction, the slurry was cooled and the product is isolated by filtration to give 12.2 kg of Compound 8.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was quenched with 5% acetic acid in water
  3. extractionThe product was extracted with MTBE
  4. concentrationthe organic layer concentrated

Sources & evidence

ORD record
ord-cf8713e7f6e14d258b9f46c08fbcd617
Source dataset
uspto-grants-2013_07
Patent number
US08497282B2

Reaction notes

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