Hydrochloric Acid → HCID 25100943, compound

HRID 1691594Notes

Reaction equation

HRID 1691594 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[C:11]([C:16]([N:18]3[CH2:24][C:23]4([CH3:26])[CH2:25][CH:19]3[CH2:20][C:21]([CH3:28])([CH3:27])[CH2:22]4)=[O:17])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)C.[OH-].[Na+].Cl>C(O)C>[CH3:26][C:23]12[CH2:25][CH:19]([N:18]([C:16]([C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:10]=3[CH:9]=[CH:8][N:7]4[CH2:6][CH2:5][C:4]([OH:29])=[O:3])=[O:17])[CH2:24]1)[CH2:20][C:21]([CH3:28])([CH3:27])[CH2:22]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25100942HCID 25100942, compound

Product 1

HCID 25100943HCID 25100943, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-indol-1-yl]-propionic acid ethyl ester (25 mg, 0.063 mmol) in ethanol (1 mL) was added 1N aqueous sodium hydroxide solution (1 mL), and the resulting solution stirred for 2 h. The solution was acidified with 1N hydrochloric acid solution before the organic volatiles were removed in vacuo and the aqueous residues were extracted with DCM (3×5 mL). The combined organic phases were dried (MgSO4), filtered, and evaporated in vacuo. The resulting solid was purified by preparative HPLC, dried in vacuo at 50° C. affording 10 mg (43%) of the title compound as a solid. MS-ESI m/z 369; 1H NMR (400 MHz, DMSO) δ 0.81-0.99 (m, 6H), 1.08-1.10 (m, 4H), 1.18-1.22 (m) and 1.50-1.54 (m, 1H), 1.30-1.36 (m, 3H), 1.71-1.73 (m, 1H), 2.24-2.28 (m) and 3.02-3.12 (m, 1H), 2.65 (t, 2H), 3.29 (dd) and 3.68 (dd, 1H), 3.93-3.95 (m) and 4.60-4.62 (m, 1H), 4.29 (t, 2H), 6.24-6.29 (m, 1H), 6.94-6.96 (m, 1H), 7.00-7.12 (m, 2H), 7.27 (d, 1H).

Workup

  1. customwere removed in vacuo
  2. extractionthe aqueous residues were extracted with DCM (3×5 mL)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resulting solid was purified by preparative HPLC
  7. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-a87cedb08b1d402daa371fe562f0cee8
Source dataset
uspto-grants-2012_04
Patent number
US08153798B2

Reaction notes

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