Hydrochloric Acid → HCID 86741094, compound

HRID 1731317Notes

Reaction equation

HRID 1731317 reaction equation
CN1CCOCC1.[C:8]([C:11]1[CH:27]=[CH:26][C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[S:24]=[O:25])[C:21]([OH:23])=O)=[C:13]([CH2:28][CH:29]=[CH2:30])[C:12]=1[OH:31])(=[O:10])[CH3:9].ClC(OCC(C)C)=O.[CH3:40][N:41]([CH3:45])[CH2:42][CH2:43][NH2:44].Cl>O.ClCCl.O1CCCC1>[CH3:40][N:41]([CH3:45])[CH2:42][CH2:43][NH:44][C:21](=[O:23])[C:20](=[S:24]=[O:25])[CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:14]1[CH:26]=[CH:27][C:11]([C:8](=[O:10])[CH3:9])=[C:12]([OH:31])[C:13]=1[CH2:28][CH:29]=[CH2:30]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 66053N,N-DimethylethylenediamineHCID 20228818HCID 20228818, compound

Product 1

HCID 86741094HCID 86741094, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

0.31 g. (3 mmol) N-methylmorpholine is added to a suspension of 1.06 g. (3 mmol) 3-[3-(4-acetyl-2-allyl-3-hydroxyphenoxy)-propyl]-sulphinylpropionic acid in 20 ml. dichloromethane and 10 ml. tetrahydrofuran, the reaction mixture is cooled to -10° C. and, at this temperature, 0.43 g. (3 mmol) isobutyl chloroformate, dissolved in 5 ml. dichloromethane, is added dropwise thereto. Subsequently, the reaction mixture is stirred for 15 minutes at -10° C. and then 0.26 g. (3 mmol) N,N-dimethylethylenediamine, dissolved in 5 ml. dichloromethane, is added dropwise thereto in such a manner that the temperature does not exceed -10° C. The reaction mixture is stirred for 1 hour at -10° C. and for 2 hours at 0° C. and then allowed to warm up to ambient temperature. The reaction mixture is mixed with water, acidified with 2N hydrochloric acid and the aqueous phase separated off and extracted twice with dichloromethane. The aqueous phase is then rendered alkaline with 2N aqueous sodium hydroxide solution, extracted three times with dichloromethane and the extracts washed neutral with water, dried and evaporated. The crude product is dissolved in methanol/dichloromethane and, by the addition of ethereal hydrochloric acid, 3-[3-(4-acetyl-2-allyl-3-hydroxyphenoxy)-propyl]-sulphinylpropionic acid (2-dimethylaminoethyl)-amide precipitated out as the hydrochloride. Yield 0.85 g. (67% of theory) as deliquescent crystals.

Workup

  1. customdoes not exceed -10° C
  2. stirringThe reaction mixture is stirred for 1 hour at -10° C. and for 2 hours at 0° C.
  3. temperatureto warm up to ambient temperature
  4. customthe aqueous phase separated off
  5. extractionextracted twice with dichloromethane
  6. extractionextracted three times with dichloromethane
  7. washthe extracts washed neutral with water
  8. customdried
  9. customevaporated
  10. dissolutionThe crude product is dissolved in methanol/dichloromethane and, by the addition of ethereal hydrochloric acid, 3-[3-(4-acetyl-2-allyl-3-hydroxyphenoxy)-propyl]-sulphinylpropionic acid (2-dimethylaminoethyl)-amide
  11. customprecipitated out as the hydrochloride

Sources & evidence

ORD record
ord-0bcfe13f76e34fd2b6f3e4ed68ffada9
Source dataset
uspto-grants-1986_11
Patent number
US04621098

Reaction notes

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