HCID 67358307, compound → HCID 86658115, compound

HRID 577972Notes

Reaction equation

HRID 577972 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([C:8]2[C:21]([CH2:22][OH:23])=[CH:20][C:11]3[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][O:14][C:10]=3[C:9]=2[F:24])[CH2:5][C@H:4]([CH3:25])[O:3]1>ClCCl.[O-2].[O-2].[Mn+4].O=[Mn]=O>[CH3:1][C@@H:2]1[CH2:7][N:6]([C:8]2[C:21]([CH:22]=[O:23])=[CH:20][C:11]3[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][O:14][C:10]=3[C:9]=2[F:24])[CH2:5][C@H:4]([CH3:25])[O:3]1

Participants

5

Reactant 1

HCID 67358307HCID 67358307, compound2×

Product 1

HCID 86658115HCID 86658115, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalyst2×HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Ethyl 6-((2R,6S)-2,6-dimethylmorpholino)-7-fluoro-5-(hydroxymethyl)benzo[d]isoxazole-3-carboxylate (Intermediate 262, 430 mg, 1.22 mmol) was dissolved in dichloromethane (100 ml). Manganese dioxide (2122 mg, 24.41 mmol) was added and the reaction was stirred vigorously overnight. The reaction was incomplete so an additional 2 g of MnO2 was added and the reaction was stirred for 4 hours. The reaction was still incomplete so an additional 2 g of MnO2 was added and the reaction was stirred overnight. The reaction was filtered through celite and washed through with DCM and ethyl acetate. The filtrate was concentrated to give the title compound (350 mg, 0.999 mmol, 82%)

Workup

  1. additionwas added
  2. stirringthe reaction was stirred for 4 hours
  3. additionwas added
  4. stirringthe reaction was stirred overnight
  5. filtrationThe reaction was filtered through celite
  6. washwashed through with DCM and ethyl acetate
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e8fe491657d64e3088a923b25048da20
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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