Hydrochloric Acid → N-[(Phenylmethoxy)-carbonyl]-D-phenylalanyl-L-proline Methyl Ester

HRID 1080840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1080840
[C:1]([NH:11][C@@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:23][O:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1.Cl.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C.O>[CH3:23][O:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:20](=[O:22])[C@@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Komponenten

8

Edukt 5

HCID 313Hydrochloric Acid2×HCID 79724-MethylmorpholineHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanineHCID 853477Methyl L-prolinateHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 54358369N-[(Phenylmethoxy)-carbonyl]-D-phenylalanyl-L-proline Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-CBZ-D-phenylalanine (47.3 g, 0.158 mmol) in DMF (300 mL) at 0° C., was added L-proline-methylester.HCl (25.0 g, 0.151 mmol), 1-hydroxybenzotriazole hydrate (20.28 g, 0.166 mmol), ethyl-3-(3-dimethylamino)-propyl carbodiimide.HCl (31.8 g, 0.166 mmol) and 4-methylmorpholine (16.0 g, 0.159 mmol). The reaction mixture was stirred for 8 h while allowing the reaction to warm to room temperature. The reaction mixture was poured in water (1.2 L) and extracted with ethyl acetate (3×300 mL). The combined organic extracts were washed as follows: KHSO4 (0.25M, 2×200 ml), water (1×200 mL), saturated aqueous NaHCO3 (2×200 ml) and saturated NaCl (1×200 mL). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo to give title compound, 60.9 g (98%), as an oil.

Aufarbeitung

  1. customthe reaction
  2. extractionextracted with ethyl acetate (3×300 mL)
  3. washThe combined organic extracts were washed
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-517f1aa3c6514a4faa1f75bb5e109501
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05583146

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