{4-[4-(3-tert-Butoxycarbonylaminopropionylamino)phenyl]butyl}carbamic acid benzyl ester → {2-[4-(4-Aminobutyl)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester
Reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:33])[CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:17][CH:16]=1)C1C=CC=CC=1>[Pd].CO>[C:29]([O:28][C:26](=[O:27])[NH:25][CH2:24][CH2:23][C:22](=[O:33])[NH:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH2:10])=[CH:16][CH:17]=1)([CH3:32])([CH3:30])[CH3:31]Participants
4
Procedure
To a degassed solution of {4-[4-(3-tert-butoxycarbonylaminopropionylamino)phenyl]-butyl}carbamic acid benzyl ester 330 (1.78 g, 3.79 mmol) and methanol (50 mL) was added 10% palladium on activated carbon (0.5 g, 50% wet). The mixture was hydrogenated for 4 hours under atmospheric hydrogen. The catalyst was filtered through a pad of Celite and the solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 6:1:0.1, v/v chloroform/methanol/concentrated ammonium hydroxide) to provide 340 (0.74 g, 58%). 1H NMR (300 MHz, CH3OD) δ 1.44 (s, 9H), 1.50 (m, 2H), 1.66 (m, 2H), 2.60 (m, 6H), 3.38 (m, 2H), 7.14 (d, 2H), 7.44 (d, 2H).
Workup
- filtrationThe catalyst was filtered through a pad of Celite
- customthe solvent was evaporated in vacuo
- customThe residue was purified by flash chromatography (silica gel, 6:1:0.1, v/v chloroform/methanol/concentrated ammonium hydroxide)
Sources & evidence
- ORD record
- ord-ce5dc25387ab481fa119d69411d8f25a
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07875619B2
Reaction notes
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