1,5-Dibromopentane → 2-(N-Benzyloxycarbonylamino)-3-[4-(5-bromopentyloxy)phenyl]propionic acid

HRID 487093

Reaktionsgleichung

Reaktionsgleichung von HRID 487093
[C:1]([NH:11][C@H:12]([C:21]([OH:23])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[H-].[Na+].[Br:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br>CO>[CH2:4]([O:3][C:1]([NH:11][CH:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][Br:26])=[CH:18][CH:19]=1)[C:21]([OH:23])=[O:22])=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 712438N-benzyloxycarbonyl-l-tyrosine

Produkt 1

HCID 190935992-(N-Benzyloxycarbonylamino)-3-[4-(5-bromopentyloxy)phenyl]propionic acidAusbeute 24,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

N-CBZ-L-tyrosine (2.06 g, 5.86 mmole) was treated with NaH (0.58 g, 12.08 mmole) and 1,5-dibromopentane (0.8 ml, 5.87 mmole) as described for 1-1 in Example 1. The crude product was dissolved in methanol and after stirring with silica gel for 0.5 hour, the solvent was removed. This was dry packed and eluted on a flash column with CHCl3 and then with 97:3:0.3 CHCl3 /CH3OH/HOAc to give pure 1-10 (0.66 g).

Aufarbeitung

  1. customthe solvent was removed
  2. customThis was dry
  3. washeluted on a flash column with CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-e10905b762ca442ba579938f67ff9895
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294616

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