Trifluoroacetic acid → N-{3-hydroxy-2-[4-(3-phenylpropoxy)benzyl]propyl}-beta-alanine

HRID 1631192Notes

Reaction equation

HRID 1631192 reaction equation
[OH:1][CH2:2][CH:3]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:18][CH:17]=1)[CH2:4][NH:5][CH2:6][CH2:7][C:8]([O:10]C(C)(C)C)=[O:9].NCCCC1C=CC(O)=CC=1.FC(F)(F)C(O)=O>ClCCl>[OH:1][CH2:2][CH:3]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:20][CH:21]=1)[CH2:4][NH:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4574248HCID 4574248, compoundHCID 23121314tert-butyl N-{3-hydroxy-2-[4-(3-phenylpropoxy)benzyl]propyl}-beta-alaninate

Product 1

HCID 23121697N-{3-hydroxy-2-[4-(3-phenylpropoxy)benzyl]propyl}-beta-alanine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-{3-hydroxy-2-[4-(3-phenylpropoxy)benzyl]propyl}-β-alaninate (65 mg; prepared by following the procedure of Example 4 using the compound prepared in Example 15 as a substitute for 4-(3-aminopropyl)phenol) in dichloromethane (3 mL), trifluoroacetic acid (3 mL) was dropped at 0° C., followed by stirring at room temperature for 2 hours. Then, the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4). The crude product thus obtained was washed with diethyl ether to give the title compound (38 mg) having the following physical properties.

Workup

  1. customprepared
  2. concentrationThen, the reaction mixture was concentrated
  3. customThe residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4)
  4. customThe crude product thus obtained
  5. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-369e197636fb4f2bb89dba1aa9693362
Source dataset
uspto-grants-2014_07
Patent number
US08791159B2

Reaction notes

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