Hydrochloric Acid → HCID 67856678, compound

HRID 484417Notes

Reaction equation

HRID 484417 reaction equation
C(OC([NH:8][C@H:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=2[Cl:19])[NH:12][C@@H:11]([C:21]([OH:23])=[O:22])[CH2:10]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[ClH:19].[NH2:8][C@H:9]1[C:18]2[C:13](=[CH:14][C:15]([Cl:20])=[CH:16][C:17]=2[Cl:19])[NH:12][C@@H:11]([C:21]([OH:23])=[O:22])[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15168501HCID 15168501, compound

Product 1

HCID 67856678HCID 67856678, compoundYield 177.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of cis-4-tertiary-butyloxycarbonylamino-2-carboxy-5,7-dichloro-1,2,3,4-tetrahydroquinoline (100 mg, 0.277 mmol) in ethyl acetate (5 ml) was added hydrogen chloride in ethyl acetate (5 ml of an approx. 5M solution) and the resulting mixture was stirred at room temperature for 2.5 h. The solvent was removed in vacuo and the residue was triturated with ethyl acetate. The solid was collected by filtration to give the title compound (0.073 g, m.p. 176°-178 g°C.); δ (360 MHz, D2O) 2.42 (1H, m, CHACHBHCCHD), 2.67 (1H, dm, J=15.6 Hz, CHACHBHCCHD 4.27 (1H, dd, J=6.6 and 1.7 Hz, CHACHBHCCHD), 4.90 (1H, dd, J=5.6 and 1.4 Hz, CHACHBHCCHD), 6.77 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.88 (1H, d, J=2.0 Hz, 6-H or 8-H); m/e (FAB) 261 (M+1); Found: C, 40.17; H, 3.79; N, 9.23. C10H10Cl2N2O3.HCl requires C, 40.36; H, 3.73; N, 9.41%.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated with ethyl acetate
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-1392089cff264779ac819d60e6a625ad
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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