Propylamine → HCID 54246754, compound

HRID 596810Notes

Reaction equation

HRID 596810 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:32]([NH2:35])[CH2:33][CH3:34]>O1CCCC1>[CH2:32]([NH:35][C:14](=[O:16])[C@@H:12]([CH3:13])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 70832N-Cbz-d-alanine

Product 1

HCID 54246754HCID 54246754, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

to a solution of 44.64 parts of benzyloxycarbonyl-D-alanine in 276 parts of tetrahydrofuran is added 2.02 parts of N-methylmorpholine. The resulting solution is cooled to about -30° C. and 25.4 parts of isobutyl chloroformate is added with stirring. After stirring for about 5 minutes, 13.0 parts of n-propylamine is added and the mixture stirred for a further 10 minutes. The mixture is cooled overnight and then concentrated under reduced pressure to a syrup. This residue is dissolved in methylene chloride and washed successively with 2 M potassium carbonate, water, twice with 1 M hydrochloric acid and finally, twice with water. After drying over anhydrous magnesium sulfate the solution is concentrated under reduced pressure. The residue is diluted with 180 parts of ethyl ether and cooled to 5° C. The resulting crystals are filtered, washed with ether and dried to give benzyloxycarbonyl-D-alanine n-propylamide, melting at about 116.5°-120° C.

Workup

  1. stirringAfter stirring for about 5 minutes
  2. stirringthe mixture stirred for a further 10 minutes
  3. temperatureThe mixture is cooled overnight
  4. concentrationconcentrated under reduced pressure to a syrup
  5. dissolutionThis residue is dissolved in methylene chloride
  6. washwashed successively with 2 M potassium carbonate, water, twice with 1 M hydrochloric acid
  7. dry with materialAfter drying over anhydrous magnesium sulfate the solution
  8. concentrationis concentrated under reduced pressure
  9. additionThe residue is diluted with 180 parts of ethyl ether
  10. temperaturecooled to 5° C
  11. filtrationThe resulting crystals are filtered
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-07de2f35c24843cf83ab54f72390f6ad
Source dataset
uspto-grants-1977_03
Patent number
US04012367

Reaction notes

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