Reaktion #1785953

ord-174104e21bf942eca47009a7ca55e65e

Reaktionsgleichung

CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(C)(C)C(=O)O)c2)CN(C2CCCCC2)c2ccccc21
(R)-(−)-2-[3-[3-(1-tert-Butylcarbonylmethyl-2-oxo-5-c yclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)urei do]phenyl]-2-methylpropionic acid
N[C@H]1CC[C@H](O)CC1
Trans-4-amino-cyclohexanol
→
CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(C)(C)C(=O)O)c2)CN(C2CCCCC2)c2ccccc21.N[C@H]1CC[C@H](O)CC1
title compound
Ausbeute 82.8%
CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(C)(C)C(=O)O)c2)CN(C2CCCCC2)c2ccccc21.N[C@H]1CC[C@H](O)CC1
(R)-2-[3-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodi azepin-3-yl)ureido]phenyl]-2-methylpropionic acid trans-4-aminocyclohexanol salt
Ausbeute 82.8%

Edukte

CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(C)(C)C(=O)O)c2)CN(C2CCCCC2)c2ccccc21
(R)-(−)-2-[3-[3-(1-tert-Butylcarbonylmethyl-2-oxo-5-c yclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)urei do]phenyl]-2-methylpropionic acid
N[C@H]1CC[C@H](O)CC1
Trans-4-amino-cyclohexanol

Reagenzien

Keine

Lösungsmittel

CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISSOLUTIONdissolved
  2. 2
    Temperaturunder heat
  3. 3
    Sonstigecrystals so precipitated
  4. 4
    Filtrationwere collected by filtration
  5. 5
    Sonstigedried

Vorschrift

(R)-(−)-2-[3-[3-(1-tert-Butylcarbonylmethyl-2-oxo-5-c yclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)urei do]phenyl]-2-methylpropionic acid (42 mg) was dissolved in acetonitrile (0.5 mL). Trans-4-amino-cyclohexanol (8 mg) was added and then dissolved under heat. After the mixture was allowed to stand overnight, crystals so precipitated were collected by filtration and dried, whereby the title compound (39 mg) was obtained. Yield: 77%.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06344452B1uspto-grants-2002_02