4-((1R)-1-Aminoethyl)phenol → (R)-N2-(Boc)-N5-(Cbz)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide

HRID 366030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 366030
[N+](C1C=CC=CC=1O[C:11](=[O:35])[C@@H:12]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O-])=O.[OH:36][C:37]1[CH:45]=[CH:44][C:40]([C@H:41]([NH2:43])[CH3:42])=[CH:39][CH:38]=1>C(Cl)Cl.CCOC(C)=O>[C:14]([NH:13][C@@H:12]([C:11]([NH:43][C@@H:41]([C:40]1[CH:44]=[CH:45][C:37]([OH:36])=[CH:38][CH:39]=1)[CH3:42])=[O:35])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

Komponenten

5

Edukt 2

HCID 146963084-((1R)-1-Aminoethyl)phenolHCID 54461433Nalpha-Boc-Ndelta-Cbz-(R)-ornithine o-nitrophenyl ester

Produkt 1

HCID 131722030(R)-N2-(Boc)-N5-(Cbz)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Nα -Boc-Nδ -Cbz-(R)-ornithine o-nitrophenyl ester (33 g; 66.8 mmol; from step (a) above) and (R)-4-hydroxy-α-methylbenzylamine (9.3 g; 68.2 mmol) were combined in CH2Cl2 (600 mL). The resulting yellow solution was stirred at room temperature for 4 hours. When the coupling was complete, as determined by TLC, the solution was concentrated under vacuum to give the crude product. The crude material was dissolved in EtOAc, washed with 0.5N NaOH (2×300 mL), saturated KHSO4 (2×300 mL), brine (2×300 mL), dried over Na2SO4, filtered and concentrated to yield 30.1 g (61.9 mmol; 93%) of the sub-title compound.

Aufarbeitung

  1. concentrationthe solution was concentrated under vacuum
  2. customto give the crude product
  3. washwashed with 0.5N NaOH (2×300 mL), saturated KHSO4 (2×300 mL), brine (2×300 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3e7a16863b624ac8b4bec986408f302e
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127414

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