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

HRID 17542Notes

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

Participants

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

customThe reaction liquid
extractionfollowed by extraction with ethyl acetate (200 ml)
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
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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