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

HRID 275875

Reaction equation

HRID 275875 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 69696794alpha-(3-Tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-(thiazol-5-yl)methylamino-benzyl alcoholYield 96.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-487c39547e64462aa5b1e8b8cd8ae5f1
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Linked notes

Loading…