4-Methylmorpholine → BOC-Ala-Gly-OBzl

HRID 1379600Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1379600
Cl.CN(C)CCCN=C=NCC.[C:13]([NH:20][C@H:21]([C:23]([OH:25])=O)[CH3:22])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[NH2:26][CH2:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[NH:20]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C@H:21]([C:23]([NH:26][CH2:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])=[O:25])[CH3:22]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 85082Tert-butoxycarbonylalanineHCID 409140Benzyl glycinateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 10980600BOC-Ala-Gly-OBzl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

One equivalent of EDC [1-(3-dimethylaminopropyl)3-ethylcarbodiimide.hydrochloride] (1 g, 5.3 mmol, Aldrich) is added into a cold stirred solution of 1 g (5.3 mmol) Boc Alanine (Sigma), 1.07 g of (5.3 mmol) of Gly-OBzl (Sigma), 0.71 g of HOBT (Aldrich), and 0.5 ml of NMM in 50 ml DCM. The reaction mixture is stirred at 0° C. for 3 h and at ambient temperature for 22 h. The precipitate is filtered out and the filtrate is diluted with 100 ml of ethyl acetate. The organic layer is washed with 10% aqueous citric acid, water, saturated NaHCO3, water, and saturated brine. The organic layer is dried over anhydrous Na2SO4 and the solid is decanted from the mixture. The organic solvent is evaporated and the residue is recrystallized using petroleum ether to give a colorless solid of Boc-Ala-Gly-OBzl (11). 1H-NMR (CDCl3): 1.35 (3H,d, J=6 Hz), 1.42 (9H, s), 4.05 (2H, d, J=5 Hz), 4.25 (1H, m), 5.15 (2H, s), 5.28 (1H, d, J=5 Hz), 7.02 (1H, br), 7.33 (5H, s). FABMS: 337 (M+1).

Aufarbeitung

  1. filtrationThe precipitate is filtered out
  2. additionthe filtrate is diluted with 100 ml of ethyl acetate
  3. washThe organic layer is washed with 10% aqueous citric acid, water, saturated NaHCO3, water, and saturated brine
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. customthe solid is decanted from the mixture
  6. customThe organic solvent is evaporated
  7. customthe residue is recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-20d19bdfe0a94f29af65ac7742dfff11
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05672584

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