Phenyl isocyanate → 2-{3-[1-tert-Butoxycarbonyl-5-(4-trimethylstannanyl-benzylamino)-pentyl]-ureido}-pentanedioic acid di-tert-butyl ester

HRID 625923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 625923
[C:1]([O:5][C:6](=[O:34])[CH:7]([NH:17][C:18]([NH:20][CH:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])=[O:19])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].C1(N=C=O)C=CC=CC=1.[CH3:44][Sn:45]([CH3:55])([CH3:54])[C:46]1[CH:53]=[CH:52][C:49]([CH:50]=O)=[CH:48][CH:47]=1>>[C:1]([O:5][C:6](=[O:34])[CH:7]([NH:17][C:18]([NH:20][CH:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:50][C:49]1[CH:52]=[CH:53][C:46]([Sn:45]([CH3:44])([CH3:55])[CH3:54])=[CH:47][CH:48]=1)=[O:19])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 3

HCID 7672Phenyl isocyanateHCID 138406964-Trimethylstannanyl-benzaldehydeHCID 744053812-[3-(5-Amino-1-tert-butoxycarbonyl-pentyl)-ureido]-pentanedioic acid di-tert-butyl ester

Produkt 1

HCID 668983092-{3-[1-tert-Butoxycarbonyl-5-(4-trimethylstannanyl-benzylamino)-pentyl]-ureido}-pentanedioic acid di-tert-butyl esterAusbeute 40 %

Versuchsvorschrift

The following compounds of the general structure 8 were prepared in overall yields ranging from 20-60% by the route depicted in Scheme B. The key synthetic intermediate (4) was reacted with the appropriate phenylisocyanate at room temperature to afford the desired protected intermediates (5) in good yields. The t-butyl ester protecting groups were removed in the presence of 50% TFA in DCM for 1 hour at room temperature. Upon completion, the reactions were concentrated on a rotary evaporator purified by HPLC or recrystallization to afford the desired products (6) in 40-90% yield.

Aufarbeitung

  1. customThe following compounds of the general structure 8 were prepared
  2. customin overall yields
  3. customto afford the
  4. customThe t-butyl ester protecting groups were removed in the presence of 50% TFA in DCM for 1 hour at room temperature
  5. concentrationUpon completion, the reactions were concentrated on a rotary evaporator
  6. custompurified by HPLC or recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-a8a023880a24413d8bfe5285ef519092
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309193B2

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