Hydrochloric Acid → 2-(1-Bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid

HRID 1357307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357307
C[O:2][C:3](=[O:41])[CH:4]([O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][N:24]([C:26](=[O:39])[C:27]3[CH:32]=[CH:31][C:30]([CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:29][CH:28]=3)[CH3:25])[CH:19]=2)[C:14]=1[Br:40])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C1COCC1>[Br:40][C:14]1[C:15]2[C:20](=[CH:19][C:18]([CH2:23][N:24]([C:26](=[O:39])[C:27]3[CH:32]=[CH:31][C:30]([CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:29][CH:28]=3)[CH3:25])=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[O:12][CH:4]([CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:3]([OH:41])=[O:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 691377602-(1-Bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester

Produkt 1

HCID 101214512-(1-Bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acidAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-(1-bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester (445 mg, 0.68 mmol), prepared in the previous step, and 0.5 mL of 10% aqueous NaOH in THF was stirred at room temperature for 2.5 h. Aqueous 10% HCl was added until acidic and the reaction extracted three times with ethyl acetate. The combined extracts were dried (Na2SO4) and the solvent removed under reduced pressure to give the title compound (419 mg, 95%), MS m/z: 600 [M+H]+.

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a950d150768c4350ab1ed9742ab8d388
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06589970B2

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