Ethanol → 1,3-Diethyl 2-[[[2-(4-amino-1H-indol-1-yl)acetyl]oxy]methyl]-2-phenylpropanedioate

HRID 1864972Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:34])[C:5]([CH2:17][O:18][C:19](=[O:33])[CH2:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([N+]([O-])=O)=[CH:22]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(O)C.O.[Cl-].[NH4+:40]>O1CCCC1>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:17][O:18][C:19](=[O:33])[CH2:20][N:21]1[C:29]2[C:24](=[C:25]([NH2:40])[CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:34])[CH3:10]

Participants

Conditions

Temperature: 100 °C

Procedure

The 2-[2-(3-Nitroindol-1-yl)acetoxymethyl]-2-phenylmalonic acid diethyl ester (100 mg) obtained in Example 9c) was dissolved in tetrahydrofuran (2 mL), ethanol (4 mL) and water (1 mL), and to the solution were added ammonium chloride (57 mg) and reduced iron (60 mg). The mixture was stirred at 100° C. for 2 hours, cooled, and filtered through a Celite pad. The filtrate was concentrated and diluted with ethyl acetate. The extract was washed successively with saturated aqueous sodium bicarbonate, water and saturated brine, dried over sodium sulfate, and concentrated to give the title compound (93 mg).

Workup

temperaturecooled
filtrationfiltered through a Celite pad
concentrationThe filtrate was concentrated
additiondiluted with ethyl acetate
washThe extract was washed successively with saturated aqueous sodium bicarbonate, water and saturated brine
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-fa5d29c7cdcc45b89f1bd4701f08b5dd
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625948B2

Reaction notes

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