Trifluoroacetic acid → 3-[4-Hydroxy-2-(2-isopropoxycarbonylamino-ethyl)-phenyl]-propionic acid methyl ester

HRID 1181088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181088
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH2:13][CH2:14][NH:15][C:16]([O:18][C:19](C)([CH3:21])[CH3:20])=[O:17].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH2:13][CH2:14][NH:15][C:16]([O:18][CH:19]([CH3:20])[CH3:21])=[O:17]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 589793153-[2-(2-Tert-butoxycarbonylamino-ethyl)-4-hydroxy-phenyl]-propionic acid methyl ester

Produkt 1

HCID 589793233-[4-Hydroxy-2-(2-isopropoxycarbonylamino-ethyl)-phenyl]-propionic acid methyl esterAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-[2-(2-tert-butoxycarbonylamino-ethyl)-4-hydroxy-phenyl]-propionic acid methyl ester (282 mg, 0.876 mmol; Example 544, Step E) in CH2Cl2 (10 mL) at ambient temperature was treated with TFA (5.0 mL), stirred for 60 min, and concentrated. The residue in CH2Cl2 (10 mL) was treated with triethyl amine (2.0 mL) and iso-propyl chloroformate (0.97 mL, 1.0 M in toluene). The reaction mixture was stirred at ambient temperature for 16 h and concentrated. The crude material was purified using silica gel chromatography (50% EtOAc/hexanes) to yield the title compound (180 mg, 67%).

Aufarbeitung

  1. concentrationconcentrated
  2. additionThe residue in CH2Cl2 (10 mL) was treated with triethyl amine (2.0 mL) and iso-propyl chloroformate (0.97 mL, 1.0 M in toluene)
  3. stirringThe reaction mixture was stirred at ambient temperature for 16 h
  4. concentrationconcentrated
  5. customThe crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-595e2578ce7f45a2a473885d9bed79ee
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282501B2

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