Hydrochloric Acid → HCID 21191889, compound

HRID 1069555Notes

Reaction equation

HRID 1069555 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][CH:19]=2)[C:7]=1[CH3:32])C.Cl>CO.[OH-].[Na+].O>[CH2:25]([O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)[C:6]([CH2:5][C:4]([OH:33])=[O:3])=[C:7]2[CH3:32])=[CH:19][CH:20]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 537001231-[(4-benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester

Product 1

HCID 21191889HCID 21191889, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-[(4-Benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid. Using the method described in Example 6, Part A, 2.0 g (8.12 mmol) of 5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester, 0.325 g (8.12 mmol) of 60% NaH/mineral oil, and 1.88 g (8.12 mmol) of 4-benzyloxy-1-chloromethylbenzene were reacted to give on workup 800 mg of crude 1-[(4-benzyloxyphenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester. The crude ester in 50 mL of MeOH and 15 mL of 1N NaOH was heated at reflux temperature for 3 hours and left standing for 16 hours. After diluting with water, the mixture was made acidic with 1N HCl and extracted with EtOAc. The EtOAc solution was dried (Na2SO4) and concentrated. The residue was crystallized from MeOH to give 280 mg (32% yield) of 1-[(4-benzyloxyphenyl)-methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid, mp, 175-179° C.

Workup

  1. temperatureat reflux temperature for 3 hours
  2. waitleft
  3. extractionextracted with EtOAc
  4. dry with materialThe EtOAc solution was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-d7a664f8bcfa4b46ad4544ec10722543
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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