Sodium Hydroxide → HCID 21099110, compound

HRID 1351735Notes

Reaction equation

HRID 1351735 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][C:6]1([CH2:24][CH2:25][CH3:26])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[C:17]([C:19](=[O:22])[NH:20][CH3:21])[CH:16]=[CH:15][C:14]=3[CH3:23])C.[OH-].[Na+]>C1COCC1.CO>[CH3:23][C:14]1[CH:15]=[CH:16][C:17]([C:19](=[O:22])[NH:20][CH3:21])=[C:18]2[C:13]=1[NH:12][C:11]1[C:6]([CH2:5][C:4]([OH:27])=[O:3])([CH2:24][CH2:25][CH3:26])[O:7][CH2:8][CH2:9][C:10]2=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69425076HCID 69425076, compound

Product 1

HCID 21099110HCID 21099110, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (8-methyl-5-methylcarbamoyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester (87 mg, 0.234 mmol) in THF/MeOH (1.5 mL/1.5 mL) was added 1 N NaOH (0.468 mL, 0.468 mmol). The reaction mixture was stirred at ambient temperature overnight. The most of THF/MeOH was removed under reduced pressure and the resulting mixture was acidified with 1 N HCl. The mixture was extracted with EtOAc (3×10 mL). The combined organic phase was washed with brine (20 mL), dried over Na2SO4 and concentrated. The residue was purified by preparative HPLC to give 67 mg (84%) of title compound as a white solid. Mp=89–91° C.; HRMS (ESI) [M+H]+ calculated for C19H25N2O4 345.1809, found 345.1807; 1H NMR (DMSO-d6): 300 MHz δ 10.63 (s, 1H), 8.00 (s, 1H), 6.97 (d, J=6.00 Hz, 1H), 6.84 (d, J=6.00 Hz, 1H), 3.89 (m, 1H), 3.81 (m, 1H), 2.93–2.46 (m, 10H), 2.01 (m, 2H), 1.29 (m, 1H), 0.82 (m, 1H), 0.78 (t, J=5.10 Hz, 3H). LCMS retention time: 1.936 minutes.

Workup

  1. customThe most of THF/MeOH was removed under reduced pressure
  2. extractionThe mixture was extracted with EtOAc (3×10 mL)
  3. washThe combined organic phase was washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1252d1e1dfc34711bf411757fc3acc45
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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