Trifluoroacetic acid → (S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide

HRID 429126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 429126
C(OC(=O)[NH:7][C@H:8]([C:24](=[O:30])[NH:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C@@H:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:15]=1)[C:24]([NH:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:30]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 15517726(S)-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 15517727(S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamideAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (S)-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-carbamic acid tert-butyl ester (6.0 g, 14.1 mmol, Example 2, Step B) in CH2Cl2 (28 mL) was treated with trifluoroacetic acid (28 mL). The resulting solution was stirred for 20 minutes and then concentrated. The residue was diluted with EtOAc (300 mL), washed with saturated bicarbonate solution (2×300 mL) and brine (300 mL), dried over Na2SO4, and concentrated to give 4.2 g (91%) of (S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide.

Aufarbeitung

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc (300 mL)
  3. washwashed with saturated bicarbonate solution (2×300 mL) and brine (300 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6f91447c936849e1a1f37f0b7a771795
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316440B1

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