(S)-tert-Butyl (1-amino-3-phenylpropan-2-yl)carbamate → Di-tert-butyl ((2R,2'S)-azanediylbis(1-phenylpropane-3,2-diyl))dicarbamate

HRID 39365Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(C)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:10][NH:11][CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

The product from Example 1B (0.54 g, 2.16 mmol) and the product from Example 1C (0.50 g, 2.14 mmol) in isopropanol (5 mL) were placed in a sealed tube and heated at 100° C. for 18 hours. The mixture was concentrated and the residue was purified by column chromatography on silica gel (24:1 CHCl3:methanol) to provide the title compound as a colorless solid (0.44 g, 42%). Rf=0.55 (CHCl3:methanol, 9:1); 1H NMR (CDCl3) δ 7.30-7.14 (m, 10H), 4.61 (br s, 2H), 3.87 (m, 2H), 2.87-2.77 (m, 2H), 2.72 (dd, J=7.4, 13.6 Hz, 2H), 2.57 (d, J=5.8 Hz, 4H), 1.41 (s, 18H); MS (APCl+) m/z 484 (M+H)+.

Workup

concentrationThe mixture was concentrated
customthe residue was purified by column chromatography on silica gel (24:1 CHCl3:methanol)

Sources & evidence

ORD record: ord-9cd035eaff7b41de8b13b0c94570674d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524753B2

Reaction notes

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