Dicyclohexylamine → HCID 20285454, compound

HRID 127629Notes

Reaction equation

HRID 127629 reaction equation
C([O:5][C:6](=[O:25])[CH2:7][N:8]([C:12](=[O:24])[CH:13]([S:15][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:14])[CH:9]1[CH2:11][CH2:10]1)(C)(C)C.C1CCC(NC2CCCCC2)CC1>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.CCOCC>[C:16]([S:15][CH:13]([CH3:14])[C:12]([N:8]([CH:9]1[CH2:11][CH2:10]1)[CH2:7][C:6]([OH:25])=[O:5])=[O:24])(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 7582DicyclohexylamineHCID 20285449HCID 20285449, compound

Product 1

HCID 20285454HCID 20285454, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

Crude N-(2-benzoylthiopropanoyl)-N-cyclopropylglycine tert-butyl ester (17.1 g) was dissolved in a mixture of anisole (25 ml) and trifluoroacetic acid (100 ml). The resulting solution was stirred at room temperature for two hours. Trifluoroacetic acid was removed in vacuo and the residue was distributed between ethyl acetate and saturated sodium bicarbonate. The aqueous bicarbonate phase was separated and washed twice with ethyl acetate and then acidified cautiously to pH 4-6 with concentrated hydrochloric acid. The precipitated product was extracted into chloroform and washed twice with water. The organic phase was dried over magnesium sulfate, filtered and evaporated to give crude product as a pale yellow oil. The product was characterized as its DCHA salt which was prepared in ether to give colorless crystals, m.p. 140°-143° C.

Workup

  1. customTrifluoroacetic acid was removed in vacuo
  2. customThe aqueous bicarbonate phase was separated
  3. washwashed twice with ethyl acetate
  4. extractionThe precipitated product was extracted into chloroform
  5. washwashed twice with water
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give crude product as a pale yellow oil
  10. customto give colorless crystals, m.p. 140°-143° C.

Sources & evidence

ORD record
ord-3095ab476a27482081e6e37ddd7d421e
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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