Sodium Hydroxide → 4'-[[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]amino]-3-(cyclohexyloxy)-4-biphenylcarboxylic acid

HRID 2078657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2078657
[C:1]([O:5][C:6]([N:8]([CH2:35][C@@H:36]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=1)[OH:37])[CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26]C)=[O:25])=[C:20]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:19]=2)=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH2:35][C@@H:36]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=1)[OH:37])[CH2:9][CH2:10][NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[C:20]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:19]=2)=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 67097299methyl 4'-[[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-ethyl]amino]-3-(cyclohexyloxy)-4-biphenylcarboxylate

Produkt 1

HCID 670977074'-[[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]amino]-3-(cyclohexyloxy)-4-biphenylcarboxylic acidAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 4′-[[2-[(tert-butoxycarbonyl)-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-ethyl]amino]-3-(cyclohexyloxy)-4-biphenylcarboxylate (125 mg) in methanol (1.750 ml) and tetrahydrofuran (0.900 ml) was added 1N aqueous sodium hydroxide solution (1.05 ml) and the mixture was stirred at room temperature for 1 day. To the reaction mixture was added 1N aqueous sodium hydroxide solution (0.900 ml) and the mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure and to the residue were added ethyl acetate (40 ml) and water (20 ml). The pH value was adjusted to 5.70 by addition of 0.1N hydrochloric acid and the separated organic layer was washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation gave 4′-[[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]amino]-3-(cyclohexyloxy)-4-biphenylcarboxylic acid (123 mg) as a yellow foam.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 3 days
  2. concentrationThe reaction mixture was concentrated under reduced pressure and to the residue
  3. additionwere added ethyl acetate (40 ml) and water (20 ml)
  4. additionThe pH value was adjusted to 5.70 by addition of 0.1N hydrochloric acid
  5. washthe separated organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration
  8. customfollowed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-094d5326020f4171bbebe2714c6e39f2
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928264B2

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