Ethyl Acetate → HCID 58031932, compound

HRID 1411446Notes

Reaction equation

HRID 1411446 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:14][CH2:13][C@@H:12]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[N:11]2[C:24]2[CH:29]=[C:28]([F:30])[C:27]([N:31]3[CH2:36][CH2:35][CH:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH2:33][CH2:32]3)=[C:26]([F:43])[CH:25]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1.C(O)C.O.[Fe]>[F:43][C:26]1[CH:25]=[C:24]([N:11]2[C@H:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH2:14][CH2:13][C@H:12]2[C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH:29]=[C:28]([F:30])[C:27]=1[N:31]1[CH2:36][CH2:35][CH:34]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:33][CH2:32]1

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 58032010HCID 58032010, compound

Product 1

HCID 58031932HCID 58031932, compoundYield 100.1%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

The product of Example 8A (197 mg, 0.337 mmol) was dissolved in a mixture of THF (3 mL), ethanol (3 mL) and water (0.5 mL), and then iron (95 mg, 1.69 mmol) and ammonium chloride (27 mg, 0.506 mmol) were added and the mixture heated at 80° C. for 3 hours. Afterwards ethyl acetate was added to the solution followed by extraction with sodium bicarbonate. The organic extract was dried, filtered and concentrated which afforded 177 mg (100%) of the title compound. MS (ESI) m/z 525 (M+H)+.

Workup

  1. extractionfollowed by extraction with sodium bicarbonate
  2. extractionThe organic extract
  3. customwas dried
  4. filtrationfiltered
  5. concentrationconcentrated which

Sources & evidence

ORD record
ord-88febae2bb46453caa65cb857ee1f4a5
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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