Trifluoroacetic acid → 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid

HRID 489056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489056
FC(F)(F)C(O)=O.IC[C:10]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][O:22][C:23](=[O:39])[C@H:24]([CH:36]([CH3:38])[CH3:37])[NH:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>ClCCl>[CH2:29]([O:28][C:26]([NH:25][C@H:24]([C:23]([O:22][CH2:21][CH2:20][O:19][C:17]1[CH:18]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:15][CH:16]=1)=[O:39])[CH:36]([CH3:38])[CH3:37])=[O:27])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 23387399iodomethyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid

Produkt 1

HCID 233875344-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-methoxybenzyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy) benzoate (10.2 g, 19.04 mmole) in dichloromethane (100 ml) was added trifluoroacetic acid (20 ml) and the mixture was stirred 3 hours at room temperature. The solution was evaporated under reduced pressure and co-evaporated two times with toluene. The product was isolated by silica gel column chromatography. Yield: 6.9 g=87%. The product may be activated and esterified direct to a drug or converted to iodomethyl 4-(2-N-benzyloxycarbonyl-L-valyloxyethoxy)-benzoic acid as described above, that is by treatment with a base, chloroiodomethane, separation and then treatment with NaI.

Aufarbeitung

  1. customThe solution was evaporated under reduced pressure
  2. customThe product was isolated by silica gel column chromatography
  3. customthat is by treatment with a base, chloroiodomethane, separation

Quellen und Nachweise

ORD-Eintrag
ord-d51e5680069b4641a1a14c3e6ec11056
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974802B2

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