Methanol → HCID 131711273, Verbindung

HRID 26329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 26329
[NH:1]([C:47]([CH3:49])=[O:48])[C@H:2]([C:12]([NH:14][C@H:15]([C:27]([NH:29][C@H:30]([C:32]([NH:34][C@H:35]([C:37]([O:39]CC1C=CC=CC=1)=[O:38])[CH3:36])=[O:33])[CH3:31])=[O:28])[CH2:16][C:17](=[O:26])[O:18]CC1C=CC=CC=1)=[O:13])[CH2:3][O:4]CC1C=CC=CC=1.CO.O.ClCl.CC1C=C(C2C=CC(N)=C(C)C=2)C=CC=1N>CCCCO.CC(O)=O.CCOC(C)=O.O.CC(O)=O>[NH:1]([C:47]([CH3:49])=[O:48])[C@H:2]([C:12]([NH:14][C@H:15]([C:27]([NH:29][C@H:30]([C:32]([NH:34][C@H:35]([C:37]([OH:39])=[O:38])[CH3:36])=[O:33])[CH3:31])=[O:28])[CH2:16][C:17](=[O:18])[OH:26])=[O:13])[CH2:3][OH:4]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 962WaterHCID 131710166HCID 131710166, VerbindungHCID 131711274HCID 131711274, Verbindung

Produkt 1

HCID 131711273HCID 131711273, VerbindungAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 20205723n-BuOH HOAc EtOAc H2OLösungsmittel

Versuchsvorschrift

Ac-Ser(Bzl)-Asp(OBzl)-Ala-Ala-OBzl (0.6 g, 0.888 mmol) was hydrogenated in a Parr apparatus at 50 psi in the presence of 0.62 g catalyst (5% Pd on BaSO4) in a solvent mixture consisting of 35 ml MeOH, 15 ml H2O, and 1 ml HOAc for 4 hours. The catalyst was filtered off and the filtrate concentrated to a smaller volume and lyophilized to give 0.38 g crude material. Tlc showed two minor contaminants in addition to the major component. The compound was then purified on a Bio-Rad AGl×2 column (3×24 cm) which was washed with 0.2 M NaOH, H2O, 0.2 M HOAc, and equilibrated with pH 8.5 buffer of 0.025 M ammonium acetate. The sample was applied at this pH and the column eluted with 250 ml each of the following acetic acid solutions in the order of: 0.25 M, 0.5 M, 1.0 M, 1.5 M, 2.0 M, 2.5 M, 3.0 M, 3.5 M, 4.0 M, and 4.5 M. The flow rate was adjusted to approximately 50 ml/hr and each 10 ml fraction was collected into an LKB fraction collector. The compound was located by spotting a 5 μl portion from each tube on silica get tlc plate (Merck 60, F-254) and developed in the solvent system of n-BuOH:HOAc:EtOAc:H2O (1:1:1:1) and then stained with chlorine-tolidine reaction. The fractions containing the major component were pooled and lyophilized twice to give 310 mg (86.3%) of the desired product; [α]D25 =-77.01° (c 1, 10% HOAc).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated to a smaller volume
  3. customto give 0.38 g crude material
  4. additionin addition to the major component
  5. customThe compound was then purified on a Bio-Rad AGl×2 column (3×24 cm) which
  6. washwas washed with 0.2 M NaOH, H2O, 0.2 M HOAc
  7. washthe column eluted with 250 ml each of the following acetic acid solutions in the order of: 0.25 M, 0.5 M, 1.0 M, 1.5 M, 2.0 M, 2.5 M, 3.0 M, 3.5 M, 4.0 M, and 4.5 M
  8. customeach 10 ml fraction was collected into an LKB fraction collector
  9. customget tlc plate (Merck 60, F-254)
  10. additionThe fractions containing the major component

Quellen und Nachweise

ORD-Eintrag
ord-b20658a30e1044f3b79ed6341eff9d19
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04148788

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