Potassium Carbonate → 2-[4-(2-Acetoxy-ethoxy)-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid

HRID 521522Notes

Reaction equation

HRID 521522 reaction equation
C[O:2][C:3]([C:5]1([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:40]([O:43][CH2:44][CH2:45]Br)(=[O:42])[CH3:41]>CN(C=O)C>[C:40]([O:43][CH2:44][CH2:45][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:14][C:5]2([C:3]([OH:2])=[O:4])[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6]2)=[O:33])=[CH:17][C:18]=1[O:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1)(=[O:42])[CH3:41]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 670762682-[4-Hydroxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl ester

Product 1

HCID 670763312-[4-(2-Acetoxy-ethoxy)-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of step 1 of example 254 (70 mg, 0.157 mmol) was dissolved in DMF (1 ml). Potassium carbonate (108 mg, 0.786 mmol) was added and subsequently 2-bromoethyl acetate (39 mg, 0.235 mmol). The mixture was stirred at room temperature for 2 h and then partitioned between EA and water. The aqueous phase was extracted with EA, and the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was purified by RP HPLC (water/ACN gradient).

Workup

  1. custompartitioned between EA and water
  2. extractionThe aqueous phase was extracted with EA
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-3dea3c5782914adcb8d1f487316d9a31
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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