Hydrochloric Acid → HCID 67690724, compound

HRID 484451Notes

Reaction equation

HRID 484451 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([NH:20][C@@H:21]2[C:30]3[C:25](=[CH:26][C:27]([Cl:32])=[CH:28][C:29]=3[Cl:31])[NH:24][C@@H:23]([C:33]([O:35][CH3:36])=[O:34])[CH2:22]2)=[O:19])=[CH:13][CH:12]=1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[ClH:31].[NH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:18]([NH:20][C@@H:21]2[C:30]3[C:25](=[CH:26][C:27]([Cl:32])=[CH:28][C:29]=3[Cl:31])[NH:24][C@@H:23]([C:33]([O:35][CH3:36])=[O:34])[CH2:22]2)=[O:19])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86747047HCID 86747047, compound

Product 1

HCID 67690724HCID 67690724, compoundYield 182.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of trans-4(4-tertiary-butyloxycarbonylaminoethylphenyl)methylcarbonylamino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline (Example 106c) (0.150 g, 0.28 mmol) in ethyl acetate (5 ml) was added a saturated solution of hydrogen chloride in ethyl acetate (5 ml) and the resulting mixture was stirred at room temperature for 40 minutes. The solvent was then removed under vacuum and the residue was triturated with hot ethyl acetate. A gummy solid was collected by filtration and this was dissolved in water and freeze dried to give the title compound as a colourless solid (0.121 g), m.p. decomposes above 200° C. δ (360 MHz, DMSO 1.65 (1H, ddd, J=13.0, 12.5 and 3.8 Hz, CHACHBHCCHD), 2.14 (1H, dm, J=13.0 Hz, CHACHBHCCHD), 2.86 (2H, m, ArCH2CH2NH3), 3.00 (2H, m, ArCH2CH2NH3), 3.36 (2H, s, NHCOCH2Ar), 3.72 (3H, s, CO2CH3), 3.97 (1H, dd, J=12.5 and 2.5 Hz, CHACHBHCCHD), 5.00 (1H, m, CHACHBHCCHDNHCO), 6.69 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.88 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.93 (1H, s, ArNH), 7.17 (2H, d, J=8.2 Hz, ArH), 7.21 (2H, d, J=8.2 Hz, ArH), 8.04 (3H, brs, NH3), 8.49 (1H, d, J=7.0 Hz, CHDNHCO); m/e 435 (M+), 198 (100%, M-NHCOCH2C6H4CH2CH2NH2, CO2CH3 and H); Found C, 51.47; H, 5.37; N, 8.60; C21H23Cl2N3O3.HCl.H2O requires C, 51.39; H, 5.34; N, 8.56%.

Workup

  1. customThe solvent was then removed under vacuum
  2. customthe residue was triturated with hot ethyl acetate
  3. filtrationA gummy solid was collected by filtration
  4. dissolutionthis was dissolved in water
  5. customfreeze dried

Sources & evidence

ORD record
ord-f31a67004351403da0a1d377ca47df01
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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