Ethyl Acetate → HCID 58031932, compound

HRID 1429266Notes

Reaction equation

HRID 1429266 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-19f3db6d236848dc805a8d60bd0a23f0
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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