Hydrochloric Acid → HCID 16723135, compound

HRID 555268Notes

Reaction equation

HRID 555268 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([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: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:12]3[CH:11]=[C:10]4[C:15](=[CH:14][CH:13]=3)[N:7]([CH2:6][CH2:5][C:4]([OH:29])=[O:3])[CH:8]=[CH:9]4)=[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 16723134HCID 16723134, compound

Product 1

HCID 16723135HCID 16723135, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[5-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-indol-1-yl]-propionic acid ethyl ester (80 mg, 0.2 mmol) in ethanol (2 mL) was added 1N aqueous sodium hydroxide solution (2 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 55 mg (74%) of the title compound as a solid. MS-ESI m/z 369; 1H NMR (400 MHz, DMSO-d6) δ 0.94 (d, 3H), 1.04 (d, 3H), 1.13-1.17 (m, 4H), 1.28-1.38 (m, 2H), 1.43-1.45 (m, 1H), 1.60-1.63 (m, 1H), 1.75-1.79 (m, 1H), 2.24-2.32 and 3.25-3.26 (m, 1H), 2.74 (t, 2H), 3.27-3.35 (m) and 3.62-3.65 (m), 1H), 4.08-4.10 and 4.62-4.63 (m, 1H), 4.39 (t, 2H), 6.47-6.48 (m, 1H), 7.17-7.23 (m, 3H), 7.70 (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-284b4ff9159f4df1a16a1d0b35ff5ba5
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

Loading…