Sarcosine → HCID 70394364, compound

HRID 1762400Notes

Reaction equation

HRID 1762400 reaction equation
[CH:1]1([C:7](=O)[CH2:8][CH2:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:12][NH:13][CH2:14][C:15]([OH:17])=[O:16].S1C=CC=C1.C([O-])(=O)C.[K+].[H][H]>CO.[Pd]>[CH3:12][N:13]([CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:8][CH2:9][CH3:10])[CH2:14][C:15]([OH:17])=[O:16]

Participants

8

Reactant 5

HCID 1088SarcosineHCID 8030ThiopheneHCID 738321-Cyclohexylbutan-1-oneHCID 517044Potassium AcetateHCID 178418361HCID 178418361, compound

Product 1

HCID 70394364HCID 70394364, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 130 parts of 1-cyclohexyl-1-butanone, 225 parts of methyl glycine, 2 parts of a solution of thiophene in methanol 4%, 960 parts of methanol and 200 parts of potassium acetate was hydrogenated overnight in a Parr apparatus with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in water and 1,1'-oxybisethane. The whole was extracted with a hydrochloric acid solution 10%. The aqueous layer was treated with a sodium hydroxide solution and the product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated, yielding 46 parts (22.4%) of methyl N-(1-cyclohexylbutyl)glycine as a residue (int. 3).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. extractionThe whole was extracted with a hydrochloric acid solution 10%
  4. additionThe aqueous layer was treated with a sodium hydroxide solution
  5. extractionthe product was extracted with 1,1'-oxybisethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-f60ea0063d3149df939d95bbfbef6ab0
Source dataset
uspto-grants-1989_05
Patent number
US04832732

Reaction notes

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