Hydrochloric Acid → HCID 86681734, compound

HRID 571321Notes

Reaction equation

HRID 571321 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[CH2:23][C:24]([O:26]C)=[O:25])[S:10]([CH3:13])(=[O:12])=[O:11])[CH2:3][CH2:2]1.C1COCC1.[OH-].[Li+].Cl>O>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[CH2:23][C:24]([OH:26])=[O:25])[S:10]([CH3:13])(=[O:12])=[O:11])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86681733HCID 86681733, compound

Product 1

HCID 86681734HCID 86681734, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-(4-(N-(2-morpholinoethyl)methylsulfonamido)-1H-indol-1-yl)acetate (1.08 g, 2.73 mmol) in a 1/1 mixture of THF and water (30 ml), lithium hydroxide (0.654 g, 27.3 mmol) was added, and the mixture reacted for 1 hour at room temperature. The mixture was acidified with aqueous 12 N HCl (pH=5) and the desired compound was extracted with EtOAc (3×50 ml). The organic phase was dried over sodium sulfate and the solvent was removed; the residue was purified by flash chromatography (DCM/MeOH 9/1) recovering 2-(4-(N-(2-morpholinoethyl)-methylsulfonamido)-1H-indol-1-yl)acetic acid (650 mg, 1.704 mmol 62.4% yield, MS/ESI+ 381.9 [MH]+).

Workup

  1. additionwas added
  2. customthe mixture reacted for 1 hour at room temperature
  3. extractionthe desired compound was extracted with EtOAc (3×50 ml)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customthe solvent was removed
  6. customthe residue was purified by flash chromatography (DCM/MeOH 9/1)

Sources & evidence

ORD record
ord-cfdcffdcc7a642d0b023edf3fc7be657
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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