1,2-Dimethoxyethane → HCID 59516436, compound

HRID 1160471Notes

Reaction equation

HRID 1160471 reaction equation
[C:1]([O:7][C:8]1[CH:9]=[C:10]([CH2:14][C@H:15]([OH:20])[C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:12][CH:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].ClC(Cl)(Cl)C(O[CH:26]([CH3:28])[CH3:27])=N.COCCOC.FC(F)(F)S(O)(=O)=O>CCCCCCC>[C:1]([O:7][C:8]1[CH:9]=[C:10]([CH2:14][C@H:15]([O:20][CH:26]([CH3:28])[CH3:27])[C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:12][CH:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62406Trifluoromethanesulfonic acidHCID 21469209Isopropyl 2,2,2-trichloroacetimidateHCID 59516434HCID 59516434, compound

Product 1

HCID 59516436HCID 59516436, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent2×

Procedure

Methyl (2S)-3-(3-pivaloyloxyphenyl)-2-hydroxypropionate (11 kg), 2,2,2-trichloro-1-isopropoxyethanimine (20 kg, 98 mol), 1,2-dimethoxyethane (10 L), and heptane (44 L) were mixed and stirred, and the resultant solution was cooled to 7° C. Trifluoromethanesulfonic acid (2.36 kg, 15.7 mol) was added dropwise to the reaction mixture over a period of 36 minutes, followed by stirring the reaction mixture at 25° C. for 19 hours. The reaction mixture was cooled to 7° C., to which heptane (66 L) was then added. The reaction mixture was then stirred for 45 minutes, followed by filtering off a white crystal of trichloroacetoamide. Water (55 L) was added to the filtrate for separating. Then, the organic layer was washed with a 5% sodium bicarbonate aqueous solution (52 L) twice and with water (55 L), followed by vacuum concentration to obtain 12.1 kg of the title compound (yield: 96%).

Workup

  1. stirringby stirring the reaction mixture at 25° C. for 19 hours
  2. additionwas then added
  3. stirringThe reaction mixture was then stirred for 45 minutes
  4. filtrationby filtering off a white crystal of trichloroacetoamide
  5. additionWater (55 L) was added to the filtrate
  6. customfor separating
  7. washThen, the organic layer was washed with a 5% sodium bicarbonate aqueous solution (52 L) twice
  8. concentrationwith water (55 L), followed by vacuum concentration

Sources & evidence

ORD record
ord-db83bb331f4f4fd98f430baf279fe45c
Source dataset
uspto-grants-2010_10
Patent number
US07816405B2

Reaction notes

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