Ethanol → HCID 67040267, compound

HRID 605217Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:45])[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:41])[NH:32][C:33]5[CH:34]=[N:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=5)=[CH:27][C:26]=4[N+:42]([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:45])[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:41])[NH:32][C:33]5[CH:34]=[N:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=5)=[CH:27][C:26]=4[NH2:42])=[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: 80 °C

Procedure

The product of Example 201A (200 mg, 0.3233 mmol), ammonium chloride (113 mg, 2.118 mmol), and iron powder (111 mg, 1.988 mmol) in a mixture of water (3 mL), ethanol (6 mL) and tetrahydrofuran (6 mL) was heated at 80° C. under a nitrogen atmosphere for 75 minutes. The reaction was cooled to room temperature, diluted with ethyl acetate (100 mL), and washed with water (2×50 mL) and brine (50 mL). The organic was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation in vacuo to give the product as a light beige solid (175 mg, 92%).

Workup

temperatureThe reaction was cooled to room temperature
washwashed with water (2×50 mL) and brine (50 mL)
dry with materialThe organic was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated by rotary evaporation in vacuo

Sources & evidence

ORD record: ord-e401686485ec4843b8f1dce219cd700b
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

Loading…