HCID 58664814, compound → {4-[4-(3-tert-Butoxycarbonylaminopropionylamino)phenyl]butyl}carbamic acid benzyl ester

HRID 254371Notes

Reaction equation

HRID 254371 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH2:12][C:13]#[C: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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].COCCOC>[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:33])[CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58664814HCID 58664814, compound

Product 1

HCID 58664815{4-[4-(3-tert-Butoxycarbonylaminopropionylamino)phenyl]butyl}carbamic acid benzyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a degassed solution of {4-[4-(3-tert-butoxycarbonylaminopropionylamino)phenyl]-but-3-ynyl}carbamic acid benzyl ester 320 (1.91 g, 4.1 mmol) and 1,2-dimethoxyethane (DME, 35 mL) was added 10% palladium on activated carbon (0.5 g, 50% wet). The mixture was hydrogenated overnight at 50 psi pressure. The catalyst was filtered through a pad of Celite and the solvent was evaporated in vacuo to provide 330 (1.78 g, 99%). 1H NMR (300 MHz, CDCl3) δ 1.42 (s, 9H), 1.58 (m, 4H), 2.59 (t, 4H), 3.17 (q, 2H), 3.47 (q, 2H), 5.18 (m, 3H), 5.58 (m, 1H), 5.70 (m, 1H), 7.07 (d, 2H), 7.33 (m, 5H), 7.49 (d, 2H).

Workup

  1. filtrationThe catalyst was filtered through a pad of Celite
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9ccc1264617446c895a973913a1ae82e
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

Loading…