[4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid 2-tert-butoxycarbonylamino-ethyl ester → [4-(4-Aminobutyl)phenoxy]acetic acid 2-tert-butoxycarbonylaminoethyl ester ethyl acetate
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12](=[O:36])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25]C(OCC2C=CC=CC=2)=O)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.C(OCC)(=O)C.ClCCl.[OH-].[OH-].[Pd+2]>[CH2:10]([O:11][C:12](=[O:36])[CH3:13])[CH3:9].[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12](=[O:36])[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][NH2:25])=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
6
Reactant 1
Product 1
Reagents, catalysts & solvents 4
Procedure
A solution of [4-(4-benzyloxycarbonylaminobutyl)phenoxy]acetic acid 2-tert-butoxycarbonylaminoethyl ester 44a (162 mg, 0.32 mmol) and acetic acid (3 drops) in ethyl acetate (3 mL) and dichloromethane (6 mL) was stirred at room temperature for 16 h under hydrogen atmosphere in the presence of palladium hydroxide on activated charcoal (80 mg, 60% wet). The catalyst was removed by suction filtration and the liquid filtrate was concentrated in vacuo to give [4-(4-aminobutyl)phenoxy]acetic acid 2-tert-butoxycarbonylaminoethyl ester ethyl acetate 45a as an off-white solid (100 mg, 84% yield) which was used directly without purification. m/z (ESI) 367 [C19H30N2O5+H]+.
Workup
- customThe catalyst was removed by suction filtration
- concentrationthe liquid filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-fd0518c0dbb448198b7849362499095f
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07399766B2
Reaction notes
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