Hydrochloric Acid → HCID 86585359, compound

HRID 1356388Notes

Reaction equation

HRID 1356388 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:13][C:14]([O:16]CC)=[O:15])[C@H:8]3[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23][C@H:7]3[C:6]=2[C:5]=1[Cl:31].Cl>O.C1COCC1>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][C@@H:7]2[C@@H:8]([N:9]([CH2:13][C:14]([OH:16])=[O:15])[C:10]3[CH:11]=[CH:12][C:4]([Cl:3])=[C:5]([Cl:31])[C:6]=32)[CH2:19][CH2:20]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86585357HCID 86585357, compound

Product 1

HCID 86585359HCID 86585359, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of KOH (0.16 g, 2.8 mmol) in H2O (10 mL) was added to a solution of tert-butyl (5aS*,10bS*)-9,10-dichloro-6-(2-ethoxy-2-oxoethyl)-1,4,5,5a,6,10b-hexahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.96 g, 2.17 mmol) in THF (15 mL). The mixture was heated at 60° C. for 2 h. The reaction was then cooled to rt, acidified with 10% aqueous HCl, and extracted with EtOAc (3×30 mL). The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated to give crude white foam (0.90 g): 1H NMR (300 MHz, CDCl3) δ 67.14 (d, J=8.3 Hz, 1H), 6.21 (d, J=8.4Hz, 1H), 4.08 (m, 1H), 3.93 (d, J=18.3 Hz, 1H), 3.76 (d, J=18.3 Hz, 1H), 3.47 (m, 5H), 2.04 (m, 4H), 1.44 (s, 9H); HRMS (FAB) calcd for C19H24CL2N2O4+H 415.1191, found 415.1198.

Workup

  1. temperatureThe reaction was then cooled to rt
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e96ae78cf83d4e09b6718644cc050523
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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