Ethanol → {4-[2-Amino-4-(5-tert-butyl-thiazol-2-ylcarbamoyl)-phenylsulfanyl]-phenyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 605190Notes

Reaction equation

HRID 605190 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:46])[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:42])[NH:32][C:33]5[S:34][C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:36][N:37]=5)=[CH:27][C:26]=4[N+:43]([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:46])[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:42])[NH:32][C:33]5[S:34][C:35]([C:38]([CH3:41])([CH3:39])[CH3:40])=[CH:36][N:37]=5)=[CH:27][C:26]=4[NH2:43])=[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

8

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 866155534-[4-(5-tert-Butyl-thiazol-2-ylcarbamoyl)-2-nitro-phenylsulfanyl]-phenyl-carbamic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 86615554{4-[2-Amino-4-(5-tert-butyl-thiazol-2-ylcarbamoyl)-phenylsulfanyl]-phenyl}-carbamic acid 9H-fluoren-9-ylmethyl esterYield 90.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

The product of Example 161C (336 mg, 0.516 mmol), ammonium chloride (181 mg, 3.382 mmol), and iron powder (177 mg, 3.175 mmol) in a mixture of water (3 mL), ethanol (6 mL) and tetrahydrofuran (6 mL) was heated at 90° C. under a nitrogen atmosphere for 1 hour. The reaction was cooled to room temperature, diluted with ethyl acetate (100 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 to give the product as a light yellow solid (290 mg, 90%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water (3×50 mL) and brine (50 mL)
  3. dry with materialThe organic was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation in vacuo

Sources & evidence

ORD record
ord-c2dd8d8c9df84f868f9f4a9e4a0c7ae2
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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