Water → 7-amino-2-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-5-yl pivalate

HRID 2239011Notes

Reaction equation

[C:1]([O:7][C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([N+:17]([O-])=O)[CH:16]=1)[NH:13][C:12]([C:20]1[S:21][CH:22]([CH:25]([O:28][CH3:29])[O:26][CH3:27])[CH2:23][N:24]=1)=[CH:11]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].O.[Cl-].[Ca+2].[Cl-].C(=O)([O-])O.[Na+]>C(O)C.[Fe]>[C:1]([O:7][C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([NH2:17])[CH:16]=1)[NH:13][C:12]([C:20]1[S:21][CH:22]([CH:25]([O:26][CH3:27])[O:28][CH3:29])[CH2:23][N:24]=1)=[CH:11]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-7-nitro-1H-indol-5-yl pivalate (4.32 g) in ethanol (100 mL) were added water (10 mL), calcium chloride (1.13 g) and iron (3.42 g), and the mixture was stirred at 90° C. for 2 hr. The mixture was allowed to cool, and basified with saturated aqueous sodium hydrogencarbonate, and the insoluble substance was filtered off. The filtrate was extracted with ethyl acetate, and the combined organic layers were washed with water and saturated brine, dried (MgSO4), and concentrated. The residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=4:1-1:3) to give the title compound (2.55 g, yield 64%) as a pale-yellow amorphous powder. MS: 392 (MH+).

Workup

temperatureto cool
filtrationthe insoluble substance was filtered off
extractionThe filtrate was extracted with ethyl acetate
washthe combined organic layers were washed with water and saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=4:1-1:3)

Sources & evidence

ORD record: ord-157f02e2d7334ee08d5e310f3a959ff0
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718798B2

Reaction notes

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