4-Methylmorpholine → HCID 53979417, compound

HRID 1600787Notes

Reaction equation

HRID 1600787 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([NH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])[C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:45][S:46]([N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1)(=[O:48])=[O:47].CN1CCOCC1>CN(C)C=O>[CH2:18]([O:17][C:15]([NH:14][C@H:10]([C:11]([N:52]1[CH2:53][CH2:54][N:49]([S:46]([CH3:45])(=[O:48])=[O:47])[CH2:50][CH2:51]1)=[O:13])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)=[O:16])[CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 7091611-(Methylsulfonyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53878343HCID 53878343, compound

Product 1

HCID 53979417HCID 53979417, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

(S)-3-(4-cyanophenyl)-2-(butyloxycarbonylamino)propionic acid(0.5 g, 1.7 mmole) was dissolved in dimethylformamide(DMF, 20 ml) and then cooled to 0° C. Then, 1-(3-dimethylaminopropyl)-3 -ethylcarbodiimide hydrochloride(EDC, 0.5g) and 1-hydroxybenzo-triazole hydrate(HOBT,0.3 g) were added to this solution and stirred until they are completely dissolved therein. To this reaction mixture were added 1-methanesulfonyl-piperazine(0.3 g) and N-methylmorpholine(0.2 ml), and then the temperature was slowly elevated to room temperature. The reaction solution was stirred for 3.5 hours. After the reaction is completed, the reaction solution was distilled under reduced pressure to remove the volatile substance and the remaining solution was diluted with ethyl acetate, washed successively with aqueous saturated sodium hydrogen carbonate solution, dilute hydrochloric acid and saturated saline, dried over anhydrous sodium sulfate, filtered and then concentrated. The residue was purified with column chromatography using ethyl acetate/hexane(6/4, by volume) as an eluent to obtain the purified title compound(0.7 g, Yield: 93%).

Workup

  1. dissolutionare completely dissolved
  2. customwas slowly elevated to room temperature
  3. stirringThe reaction solution was stirred for 3.5 hours
  4. distillationthe reaction solution was distilled under reduced pressure
  5. customto remove the volatile substance
  6. additionthe remaining solution was diluted with ethyl acetate
  7. washwashed successively with aqueous saturated sodium hydrogen carbonate solution, dilute hydrochloric acid and saturated saline
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified with column chromatography
  12. customto obtain the

Sources & evidence

ORD record
ord-b4dedad382e14997941bfeed7cd1f5fc
Source dataset
uspto-grants-1999_11
Patent number
US05977114

Reaction notes

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