4-Methylmorpholine → Cbz-Dap(Boc)-Ala-OBn

HRID 1353176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1353176
[NH:1]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@H:2]([C:12]([OH:14])=O)[CH2:3][NH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[NH2:42][C@H:43]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH3:44]>ClCCl.C(OCC)(=O)C>[NH:1]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@H:2]([C:12]([NH:42][C@H:43]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH3:44])=[O:14])[CH2:3][NH:4][C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 726858benzyl (2S)-2-aminopropanoateHCID 2756240L-N-Cbz-3-N-Boc-Amino-alanine

Produkt 1

HCID 131726457Cbz-Dap(Boc)-Ala-OBn

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Cbz-Dap(Boc)-OH (0.41 g, 1.2 mmol) was treated with a mixture of 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide methiodide (0.374 g, 1.26 mmol) and N-hydroxybenzotriazole (0.17 g, 1.26 mmol) in N-methylmorpholine (0.28 mL, 2.1 mmol) in dichloromethane. H-Ala-OBn (0.26 g, 1.2 mmol) was added to the above solution and the resulting mixture was stirred for 14 h at room temperature, then diluted with ethyl acetate (40 mL). The organic solution was washed with 10% aqueous citric acid solution (2×30 mL), saturated aqueous sodium bicarbonate solution (2×30 mL) and brine (2×30 mL). The organic layer was dried over magnesium sulfate and then concentrated in vacuo. The crude compound (247) (0.51 g) was used without further purification.

Aufarbeitung

  1. washThe organic solution was washed with 10% aqueous citric acid solution (2×30 mL), saturated aqueous sodium bicarbonate solution (2×30 mL) and brine (2×30 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude compound (247) (0.51 g) was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-3d36004113a24f3283193389f5edfbd2
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220875B2

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