Di-tert-butyl dicarbonate → HCID 67690717, compound

HRID 484456Notes

Reaction equation

HRID 484456 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([NH:14][C@@H:15]1[C:24]2[C:19](=[CH:20][C:21]([Cl:26])=[CH:22][C:23]=2[Cl:25])[NH:18][C@@H:17]([C:27]([O:29]C)=[O:28])[CH2:16]1)=[O:13])=[N+]=[N-].C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C>C(OCC)(=O)C.[Pd]>[ClH:25].[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([NH:14][C@@H:15]1[C:24]2[C:19](=[CH:20][C:21]([Cl:26])=[CH:22][C:23]=2[Cl:25])[NH:18][C@@H:17]([C:27]([OH:29])=[O:28])[CH2:16]1)=[O:13]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 86747048HCID 86747048, compound

Product 1

HCID 67690717HCID 67690717, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trans-4-(2-azidomethylphenyl)methylcarbonylamino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline (0.3 g, 0.67 mmol) in ethyl acetate (30 ml) was added ditertiary-butyldicarbonate (0.22 g, 1.0 mmol) and 10% palladium on carbon and this mixture was hydrogenated under 50 psi pressure for 18 hours. The mixture was filtered and the solvent was removed under vacuum to yield the crude product, which was purified by flash chromatography (using ethyl acetate in hexane as eluent) followed by recrystallisation from ethyl acetate/hexane to give the title compound, m.p. 224°-225° C.; δ (360 MHz, DMSO) 1.38 (1H, ddd, J=13.2, 12.6 and 3.8 Hz, CHACHBHCCHD), 2.18 (1H, dm, J=13.2 Hz, CHACHBHCCHD), 3.50 (2H, s, NHCOCH2Ar), 3.73 (3H, s, CO2CH3), 3.95 (1H, dd, J=12.6 Hz, CHACHBHCCHD), 4.17 (2H, d, J=5.7 Hz, ArCH2NH), 5.00 (1H, m, CHACHBHCCHD), 6.70 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.87 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.92 (1H, s, ArNH), 7.19 (4H, m, ArH), 8.50 (1H, d, J=6.9 Hz, CHDNHCOCH2); m/e (EI+) 522 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed under vacuum
  3. customto yield the crude product, which
  4. customwas purified by flash chromatography (using ethyl acetate in hexane as eluent)
  5. customfollowed by recrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b00fcbf4e8ce4babbafc8f5d8c3ae390
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

Loading…