Trifluoroacetic acid → D-Phe-Pro-OBn.TFA

HRID 726652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 726652
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:10]([N:12]1[CH2:26][CH2:25][CH2:24][C@H:13]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(OC)C=CC=CC=1.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>ClCCl>[NH2:1][C@@H:2]([C:10]([N:12]1[CH2:26][CH2:25][CH2:24][C@H:13]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:42][C:43]([C:44]([OH:46])=[O:45])([F:48])[F:47]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 11155205Boc-(D)Phe-Pro-OBzl

Produkt 1

HCID 131720381D-Phe-Pro-OBn.TFAAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of Boc-D-Phe-Pro-OBn (68 g, 150 mmol) in dichloromethane (50 mL) at 0° C., was added anisole (20 mL) followed by trifluoroacetic acid (400 mL). After stirring for 3 hours, the solvents were evaporated in vacuo and the thick oily residue was dissolved in diethyl ether (1.5 L) and refrigerated (72 hours). The white precipitate was filtered, washed with diethyl ether (300 to yield dried to yield 59.4 g (85%) of white powder.

Aufarbeitung

  1. customthe solvents were evaporated in vacuo
  2. dissolutionthe thick oily residue was dissolved in diethyl ether (1.5 L)
  3. custom(72 hours)
  4. filtrationThe white precipitate was filtered
  5. washwashed with diethyl ether (300
  6. customto yield
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-40528af4aa564b9cbe22e4dd445ae728
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05710130

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