Hydrochloric Acid → HCID 10547872, compound

HRID 2292769Notes

Reaction equation

HRID 2292769 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH3:18])=[C:5]2[CH2:19][C:20]([OH:22])=[O:21].[H-].[Na+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].Cl>C1COCC1.CS(C)=O>[C:27]([CH2:26][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH3:18])=[C:5]2[CH2:19][C:20]([OH:22])=[O:21])([O:29][CH2:30][CH3:31])=[O:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 10637623HCID 10637623, compound

Product 1

HCID 10547872HCID 10547872, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 590 mg (2.0 mmol) of 5-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid (Example 2, Part C) in 30 mL of THF and 10 mL of DMSO was treated with 180 mg (4.5 mmol) of 60% NaH/mineral oil and after 10 minutes, 0.25 mL (2.25 mmol) of ethyl 2-bromoacetate was added. The mixture was stirred for 0.5 hour, acidified with 1N HCl and extracted with EtOAc. The EtOAc solution was washed with water, saturated NaCl solution, dried (Na2SO4) and concentrated at reduced pressure. After chromatography on silica (eluted with a gradient, CH2Cl2 →3% MeOH/CH2Cl2) there was obtained 590 mg (77% yield) of 5-(carbethoxymethoxy)-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid.

Workup

  1. extractionextracted with EtOAc
  2. washThe EtOAc solution was washed with water, saturated NaCl solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. washAfter chromatography on silica (eluted with a gradient, CH2Cl2

Sources & evidence

ORD record
ord-b42e770f07a248cc890aded0a39312f2
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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