Potassium bisulfate → alpha-(3-Tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-(thiazol-5-yl)methylamino-benzyl alcohol

HRID 275875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275875
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[CH:4]([OH:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=1.[CH:26]1[N:30]=[CH:29][S:28][C:27]=1[CH:31]=O.[BH4-].C([Na])#N.S([O-])(O)(=O)=O.[K+]>CO.C(O)(=O)C>[C:16]([O:15][C:13]([NH:12][CH2:11][C:7]1[CH:6]=[C:5]([CH:4]([OH:20])[C:3]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:2]=2[NH:1][CH2:31][C:27]2[S:28][CH:29]=[N:30][CH:26]=2)[CH:10]=[CH:9][CH:8]=1)=[O:14])([CH3:18])([CH3:19])[CH3:17]

Komponenten

7

Edukt 4

HCID 516920Potassium bisulfateHCID 27735771,3-Thiazole-5-carbaldehydeHCID 543588652-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholHCID 178511851HCID 178511851, Verbindung

Produkt 1

HCID 69696794alpha-(3-Tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-(thiazol-5-yl)methylamino-benzyl alcoholAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In methanol (10 ml) were dissolved 2-amino-α-(3-tert-butoxycarbonylaminomethylphenyl)-5-chlorobenzyl alcohol (1 g) produced in Example (1) and thiazole-5-carboxyaldehyde (0.34 g). To the solution were added acetic acid (0.33 g) and cyano sodium borohydride (0.21 g). The mixture was stirred for one hour at 60° C. The reaction mixture was added to a 5% aqueous solution of potassium hydrogensulfate, followed by extraction with ethyl acetate (50 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give α-(3-tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-(thiazol-5-yl)methylamino-benzyl alcohol (1.22 g) as a colorless amorphous solid product.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate (50 ml)
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by means of a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-487c39547e64462aa5b1e8b8cd8ae5f1
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352982B1

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