Methyl dichloroacetate → HCID 11417514, compound

HRID 901078Notes

Reaction equation

HRID 901078 reaction equation
[Cl:1][CH:2]([Cl:7])[C:3](OC)=[O:4].C(N(CC)CC)C.[NH2:15][C@H:16]([CH2:30][F:31])[C@@H:17]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH2:28][F:29])(=[O:27])=[O:26])=[CH:21][CH:20]=1)[OH:18]>CO>[F:31][CH2:30][C@@H:16]([NH:15][C:3](=[O:4])[CH:2]([Cl:1])[Cl:7])[C@@H:17]([C:19]1[CH:20]=[CH:21][C:22]([S:25]([CH2:28][F:29])(=[O:27])=[O:26])=[CH:23][CH:24]=1)[OH:18]

Participants

5

Reactant 3

HCID 8315Methyl dichloroacetateHCID 8471TriethylamineHCID 59699472HCID 59699472, compound

Product 1

HCID 11417514HCID 11417514, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl dichloroacetate (23.2 g, 5 eq ) and triethylamine (33.0 g, 10 eq) was added to a solution of 17 (8.64 g) in 50 ml of MeOH at room temperature. The reaction mixture was stirred overnight. Methanol was removed in vacuo. The residue was dissolved in 250 ml of ethyl acetate and washed with 1N HCl. The organic layer was washed with a 10% solution of sodium bicarbonate and brine and dried over sodium sulfate and concentrated to dryness. After purification via a column, 11.7 g of the desired product was obtained as a white solid.

Workup

  1. customMethanol was removed in vacuo
  2. dissolutionThe residue was dissolved in 250 ml of ethyl acetate
  3. washwashed with 1N HCl
  4. washThe organic layer was washed with a 10% solution of sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness
  7. customAfter purification via a column

Sources & evidence

ORD record
ord-ffc8cf722dac42a8805416f249ec1b12
Source dataset
uspto-grants-2008_04
Patent number
US07361689B2

Reaction notes

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