4-Methylmorpholine → Boc-3-cyano-(L)-phenylalanine-4-methylsulfonylpiperazide

HRID 974948

Reaktionsgleichung

Reaktionsgleichung von HRID 974948
Cl.[CH3:2][S:3]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:5])=[O:4].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.[C:29]([NH:36][C@H:37]([C:47](O)=[O:48])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([C:45]#[N:46])[CH:40]=1)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.C1COCC1>[CH3:2][S:3]([N:6]1[CH2:11][CH2:10][N:9]([C:47](=[O:48])[C@H:37]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]#[N:46])[CH:40]=2)[NH:36][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[CH2:8][CH2:7]1)(=[O:5])=[O:4]

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2734498(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(3-cyanophenyl)propanoic acidHCID 162656121-Methanesulfonylpiperazine hydrochloride

Produkt 1

HCID 131719883Boc-3-cyano-(L)-phenylalanine-4-methylsulfonylpiperazide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4.92 g (24.5 mmol) of 1-methylsulfonylpiperazine hydrochloride and 2.7 ml (24.5 mmol) of NMM was dissolved in 50 ml of DMF. After addition of 4 g (29.6 mmol) of HOBt and a solution of 5.93 g (20.4 mmol) of Boc-3-cyano-(L)-phenylalanine in 200 ml of THF, the mixture was cooled to O° C. 5.1 g (24.7 mmol) of DCC were added and the mixture was stirred for 48 hours at room temperature. Afterwards, the precipitated dicyclohexyl urea was filtered off, the THF moiety of the solution evaporated under reduced pressure, filtered and the filtrate poured into a mixture of 100 ml of 5% sodium bicarbonate solution and 200 ml of ice water. The formed precipitate was filtered off, washed with water, dissolved in methanol and the solvent was evaporated under reduced pressure. To remove the still present water, a co-distillation with toluene/isopropanol was performed several times. The only slightly impure product was processed in this form. Yield: 7.9 g (89%)

Aufarbeitung

  1. filtrationAfterwards, the precipitated dicyclohexyl urea was filtered off
  2. customthe THF moiety of the solution evaporated under reduced pressure
  3. filtrationfiltered
  4. additionthe filtrate poured into a mixture of 100 ml of 5% sodium bicarbonate solution and 200 ml of ice water
  5. filtrationThe formed precipitate was filtered off
  6. washwashed with water
  7. dissolutiondissolved in methanol
  8. customthe solvent was evaporated under reduced pressure
  9. customTo remove the still present water

Quellen und Nachweise

ORD-Eintrag
ord-4bd99622e3064d3ea1dfc1bbd73f19fe
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05607937

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