Hydrochloric Acid → (R)-N2-(Boc)-N5-(Cbz)-(R)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]ornithine amide

HRID 366068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 366068
[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.Cl.[CH3:37][O:38][C:39]1[CH:48]=[CH:47][C:42]([C@@H:43]([NH2:46])[CH2:44][OH:45])=[CH:41][CH:40]=1.CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.[Cl-].[Na+].O.O.C(N(CC)CC)C>[C:14]([NH:13][C@@H:12]([C:11]([NH:46][C@H:43]([C:42]1[CH:47]=[CH:48][C:39]([O:38][CH3:37])=[CH:40][CH:41]=1)[CH2:44][OH:45])=[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

9

Edukt 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 54461433Nalpha-Boc-Ndelta-Cbz-(R)-ornithine o-nitrophenyl esterHCID 70139936(R)-2-Amino-2-(4-methoxyphenyl)ethanol hydrochloride

Produkt 1

HCID 131722075(R)-N2-(Boc)-N5-(Cbz)-(R)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]ornithine amideAusbeute 112,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Prepared according to the method described in Example 11(a) above from Nα -Boc-Nδ -Cbz-(R)-ornithine o-nitrophenyl ester (3.11 g; 6.38 mmol; see Example 4(a) above), (R)-4-methoxy-α-hydroxymethylbenzylamine hydrochloride (1.43 g; 7.02 mmol) and triethylamine (0.97 g; 9.57 mmol; instead of DiPEA) in CH2Cl2 (100 mL), 18 hours reaction time. The reaction mixture was submitted to aqueous work up using water, 1N HCl and brine, then dried, filtered and concentrated to give a yellow solid (3.69 g) which was used without purification.

Aufarbeitung

  1. customPrepared
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-691e708adf1d46d8832cf18464133711
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127414

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