Glycine ethyl ester → Ethyl 4-(8-cyclohexyloctylamino)hippurate

HRID 903418Notes

Reaction equation

HRID 903418 reaction equation
Cl.[CH:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O1CCOCC1.[NH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].CN(C1C=CC=CN=1)C>C(N(CC)CC)C.C(Cl)Cl>[CH:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:25]=[CH:24][C:20]([C:21](=[O:22])[NH:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:19][CH:18]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 12176Glycine ethyl esterHCID 218852-DimethylaminopyridineHCID 312751,4-DioxaneHCID 20475769p-(8-Cyclohexyloctyl)aminobenzoyl chloride hydrochloride

Product 1

HCID 20475823Ethyl 4-(8-cyclohexyloctylamino)hippurate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 18.0 g. of 4-(8-cyclohexyloctylamino)benzoyl chloride hydrochloride in 100 ml. of dioxane is added to freshly prepared ethyl glycinate in 300 ml. of CH2Cl2 containing 1 g. of dimethylaminopyridine and 10 ml. of triethylamine. After 16 hours at room temperature the reaction mixture was refluxed for 2 hours, cooled and filtered. The mother liquor is extracted with water and 10% hydrochloric acid. The solution is dried over magnesium sulfate and concentrated in vacuo to an amber liquid. A 6 g. sample is pre-absorbed on 30 g. of silica III and placed on 250 ml. of alumina and eluted with ether giving 4.2 g. of solid. Thin-layer chromatography (hexane:ethylacetate, 3:1) indicates three components so this material (3 g.) is chromatographed on silica giving a solid which is recrystallized from acetonitrile to yield the product.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. extractionThe mother liquor is extracted with water and 10% hydrochloric acid
  4. dry with materialThe solution is dried over magnesium sulfate
  5. concentrationconcentrated in vacuo to an amber liquid
  6. customsample is pre-absorbed on 30 g
  7. washof alumina and eluted with ether giving 4.2 g
  8. customis chromatographed on silica giving a solid which
  9. customis recrystallized from acetonitrile
  10. customto yield the product

Sources & evidence

ORD record
ord-e049fe5607424230b187cbb529de57e1
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

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