Ethyl Acetate → HCID 66750773, compound

HRID 643943Notes

Reaction equation

HRID 643943 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([OH:13])=[O:12])[NH:8]2)=[CH:4][C:3]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].[CH2:33](O)[CH2:34][CH:35]([CH3:37])[CH3:36]>S(=O)(=O)(O)O>[CH3:36][CH:35]([CH3:37])[CH2:34][CH2:33][O:12][C:11]([C:7]1[NH:8][C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:2]([NH2:1])[CH:10]=2)=[O:13]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 31260Isoamyl AlcoholHCID 516892Sodium BicarbonateHCID 66750779HCID 66750779, compound

Product 1

HCID 66750773HCID 66750773, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
115 °C

Procedure

6-Amino-5-benzyloxy-1H-indole-2-carboxylic acid is suspended in isopentanol (10 mL) and concentrated sulfuric acid (10 drops) is added. The mixture is stirred at 115° C. for 10 min and then stirred at 90° C. for 3 h. Ethyl acetate is added and the mixture is neutralized with saturated sodium bicarbonate. The mixture is then washed with saturated NaCl (3×) and water (1×), dried over MgSO4, filtered, and concentrated to afford 6-amino-5-benzyloxy-1H-indole-2-carboxylic acid 3-methyl-butyl ester.

Workup

  1. stirringstirred at 90° C. for 3 h
  2. washThe mixture is then washed with saturated NaCl (3×) and water (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f97b50754b9a41a8b94d6594c89432ff
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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