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

HRID 430803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 430803
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 1, Step A) 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-66af52d3926d44c297157fd5e012dba4
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06323243B1

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