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HCID 68587572, compound → Methyl 4-amino-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylate

HRID 17542
Notes
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Reaction equation

HRID 17542 reaction equation
C([NH:4][C:5]1[C:10]2[CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[O:13][C:9]=2[C:8]([C:18]([O:20][CH3:21])=[O:19])=[CH:7][C:6]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)C.C(=O)([O-])O.O1CCOCC1.O.C(=O)(O)[O-].[Na+]>CO>[NH2:4][C:5]1[C:10]2[CH:11]=[C:12]([C:14]([CH3:16])([CH3:17])[CH3:15])[O:13][C:9]=2[C:8]([C:18]([O:20][CH3:21])=[O:19])=[CH:7][C:6]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 68587572HCID 68587572, compoundHCID 86585896Sodium bicarbonate waterHCID 86630873HCID 86630873, compound

Product 1

HCID 68584743Methyl 4-amino-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylateYield 48.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A methanol (60 ml) solution of methyl 4-acetylamino-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylate (I-253) (2.28 g, 6.24 mmol) and 4 N hydrogen carbonate/1,4-dioxane solution (15.6 ml, 62.4 mmol) were stirred overnight at room temperature, then heated up to 50° C. and stirred for 5 hours. The reaction liquid was put into saturated sodium bicarbonate water (300 ml), followed by extraction with ethyl acetate (200 ml). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→1:1) to obtain the entitled compound (972 mg, 48%) as a yellow white solid. Starting material recovery, 1.10 g (48%).

Workup

  1. customThe reaction liquid
  2. extractionfollowed by extraction with ethyl acetate (200 ml)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→1:1)

Sources & evidence

ORD record
ord-3a730f4d61294b44848c7111130bc563
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes