Ethanol → HCID 67040187, compound

HRID 605197Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:43])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([C:31](=[O:39])[NH:32][C:33]5[S:37][N:36]=[C:35]([CH3:38])[CH:34]=5)=[CH:27][C:26]=4[N+:40]([O-])=O)=[CH:20][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+].C(O)C.O1CCCC1>O.C(OCC)(=O)C.[Fe]>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:43])[NH:17][C:18]3[CH:19]=[CH:20][C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([C:31](=[O:39])[NH:32][C:33]5[S:37][N:36]=[C:35]([CH3:38])[CH:34]=5)=[CH:27][C:26]=4[NH2:40])=[CH:22][CH:23]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The product of Example 167A (200 mg, 0.328 mmol), ammonium chloride (115 mg, 2.152 mmol), and iron powder (113 mg, 2.021 mmol) in a mixture of water (2 mL), ethanol (4 mL) and tetrahydrofuran (4 mL) was heated at 90° C. under a nitrogen atmosphere for 1 hour. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL), and washed with water (3×50 mL) and brine (50 mL). The organic was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation in vacuo. Purification by silica gel chromatography eluting with 5% methanol/methylene chloride afforded the product as a gold-colored solid (114 mg, 60%).

Workup

temperatureThe reaction was cooled to room temperature
washwashed with water (3×50 mL) and brine (50 mL)
dry with materialThe organic was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated by rotary evaporation in vacuo
customPurification by silica gel chromatography
washeluting with 5% methanol/methylene chloride

Sources & evidence

ORD record: ord-0047ccb690ff49d89d2795dd1740c3b1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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