Hydrochloric Acid → HCID 86674998, compound

HRID 877940Notes

Reaction equation

HRID 877940 reaction equation
CS(O)(=O)=[O:3].[Cl:6][CH2:7][C@@H:8]([O:12][Si](C)(C)C)[CH2:9][C:10]#N.[CH3:17][CH2:18][O:19][C:20]([CH2:22]Br)=[O:21].Cl>O1CCCC1.[Zn]>[Cl:6][CH2:7][C@@H:8]([OH:12])[CH2:9][C:10](=[O:3])[CH2:22][C:20]([O:19][CH2:18][CH3:17])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6395Methanesulfonic AcidHCID 7748Ethyl bromoacetateHCID 11217746HCID 11217746, compound

Product 1

HCID 86674998HCID 86674998, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
27.5 °C

Procedure

Mixture of zinc dust (69 grams) and methane sulfonic acid (6 ml) in tetrahydrofuran (500 ml) was heated to reflux temperature and stirred for an hour. (S)-4-chloro-3-(trimethylsilyloxy)butanenitrile (100 grams) followed by ethyl bromo acetate (147.2 grams) was added to the reaction mixture at 65-70° C. and stirred. After completion of the reaction, the reaction mixture was cooled to 25-30° C. and then added to the aqueous hydrochloric acid solution at 0° C. and stirred. The reaction mixture extracted into ethyl acetate and then washed it with sodium bicarbonate solution followed by sodium chloride solution. Ethyl acetate was distilled off from the reaction mixture under reduced pressure to get the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature
  3. additionwas added to the reaction mixture at 65-70° C.
  4. stirringstirred
  5. customAfter completion of the reaction
  6. stirringstirred
  7. extractionThe reaction mixture extracted into ethyl acetate
  8. washwashed it with sodium bicarbonate solution
  9. distillationEthyl acetate was distilled off from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-f4570ec1568345d79f762e4f85664765
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

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