Tert-butoxycarbonylalanine → HCID 22894895, Verbindung

HRID 636203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636203
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.[C:14]([O:18][C:19](=[O:34])[C@H:20]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[NH:21][C:22](=[O:26])[C@H:23]([CH3:25])[NH2:24])([CH3:17])([CH3:16])[CH3:15].C(N[C@H](C(O)=O)C)(OC(C)(C)C)=O.Cl.C(OC(=O)[C@H](CC1C=CC=CC=1)N)(C)(C)C>CO.C(Cl)(Cl)Cl>[C:14]([O:18][C:19](=[O:34])[C@H:20]([CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[NH:21][C:22](=[O:26])[C@H:23]([CH3:25])[NH:24][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=1)([CH3:15])([CH3:16])[CH3:17]

Komponenten

6

Edukt 4

HCID 85082Tert-butoxycarbonylalanineHCID 1454243,5-Difluorophenylacetic acidHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)HCID 69622800N-(L-alaninyl)-L-phenylalanine tert-butyl ester hydrochloride

Produkt 1

HCID 22894895HCID 22894895, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

Following General Procedure C and using 3,5-difluorophenylacetic acid (Oakwood) and N-(L-alaninyl)-L-phenylalanine tert-butyl ester hydrochloride (prepared from N-BOC-L-alanine (Sigma) and L-phenylalanine tert-butyl ester hydrochloride (Advanced Chemtech) using General Procedure C, followed by removal of the BOC-group using General Procedure P), the title compound was prepared as a gel. The reaction was monitored by tlc (Rf=0.5 in 4% MeOH/CHCl3) and the product was purified by silica gel chromatography using 4% MeOH/CHCl3 as the eluent.

Aufarbeitung

  1. customfollowed by removal of the BOC-group
  2. customwas prepared as a gel
  3. customthe product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f7e9c2039d534bc3ad26613b0134870c
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06191166B1

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