Methyl dichloroacetate → HCID 11417514, compound

HRID 901081Notes

Reaction equation

HRID 901081 reaction equation
[NH2:1][C@H:2]([CH2:16][F:17])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:14][F:15])(=[O:13])=[O:12])=[CH:7][CH:6]=1)[OH:4].[Cl:18][CH:19]([Cl:24])[C:20](OC)=[O:21].C(N(CC)CC)C>CO>[F:17][CH2:16][C@@H:2]([NH:1][C:20](=[O:21])[CH:19]([Cl:24])[Cl:18])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH2:14][F:15])(=[O:13])=[O:12])=[CH:9][CH:10]=1)[OH:4]

Participants

5

Reactant 3

HCID 8315Methyl dichloroacetateHCID 8471TriethylamineHCID 59699472HCID 59699472, compound

Product 1

HCID 11417514HCID 11417514, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 17 (0.90 g, 3.39 mmol), methyl dichloroacetate (0.42 mL, 4.07 mmol) and triethylamine (0.71 mL, 5.09 mmol) in methanol (40 mL) was stirred at 40° C. for 20 hours. The reaction was quenched with water. Extraction with dichloromethane (2×100 mL) afforded an oily residue which was subjected to flash chromatography (SiO2, hexanes/ethyl acetate=2:1 to 1:1) to provide 0.98 g of the desired product as a white solid. 1H NMR (400 MHz, CDCl3) 4.28-4.38 (m, 1H), 4.46-4.72 (m, 2H), 5.05 (s, 1H ), 5.17 (s, 1H), 5.23 (t, J=4 Hz, 1H), 5.81 (s, 1H), 7.01 (d, J=8 Hz, 1H), 7.62 (d, J=8 Hz, 2H), 7.87 (d, J=8 Hz, 2H).

Workup

  1. customThe reaction was quenched with water
  2. extractionExtraction with dichloromethane (2×100 mL)
  3. customafforded an oily residue which

Sources & evidence

ORD record
ord-1b237f25427e43d394fb016b46a00ae8
Source dataset
uspto-grants-2008_04
Patent number
US07361689B2

Reaction notes

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