Benzyl-N-[5-fluoro-2-methyl-1-(3,4,5-trimethoxy-benzylidene)-3-indenylacetyl]-glycinate → 5-Fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenyl-acetic acid

HRID 1954336Notes

Reaction equation

HRID 1954336 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[CH:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)[C:6]([CH3:24])=[C:5]2[CH2:25][C:26](NCC(O)=O)=[O:27].C([O:40]C(=O)CNC(=O)CC1C2C(=CC=C(F)C=2)C(=CC2C=C(OC)C(OC)=C(OC)C=2)C=1C)C1C=CC=CC=1>C(O)C.[OH-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[CH:11][C:12]1[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)[C:6]([CH3:24])=[C:5]2[CH2:25][C:26]([OH:40])=[O:27]

Participants

6

Reactant 2

HCID 54042052Benzyl-N-[5-fluoro-2-methyl-1-(3,4,5-trimethoxy-benzylidene)-3-indenylacetyl]-glycinateHCID 57035424N-[5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetyl]-glycine

Product 1

HCID 539071775-Fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenyl-acetic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

N-[5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetyl]-glycine. Benzyl-N-[5-fluoro-2-methyl-1-(3,4,5-trimethoxy-benzylidene)-3-indenylacetyl]-glycinate (0.03 mol) in a mixture of 25 ml of anhydrous ethanol and 2.5 ml of 1 N sodium hydroxide is allowed to stand at room temperature for 18 h. The solution is diluted with water and extracted with ether. The aqueous layer is acidified with dilute hydrochloric acid and the organic product is extracted with ethyl acetate, washed with water and dried over sodium sulfate. Evaporation of the solution gives N-[5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetic acid, the corresponding indenyl acyl glycine is obtained.

Workup

  1. extractionextracted with ether
  2. extractionthe organic product is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solution

Sources & evidence

ORD record
ord-5f322a1eda9d45f5bd6cb1756c1622dc
Source dataset
uspto-grants-2000_09
Patent number
US06121321

Reaction notes

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