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

HRID 1587

Reaktionsgleichung

Reaktionsgleichung von HRID 1587
[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 mL) and 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 mL)
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-eff2bc0de6514ad8b023fb68fc66d9c2
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726159

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