Methanol → HCID 67432359, compound

HRID 245583Notes

Reaction equation

HRID 245583 reaction equation
[BH4-].[Li+].CO.[F:5][C:6]1[C:7]2[O:32][N:31]=[C:30]([N:33]3[CH:37]=[C:36]([C:38](OCC)=[O:39])[CH:35]=[N:34]3)[C:8]=2[CH:9]=[C:10]2[C:23]=1[N:22]1[CH2:24][C@@H:25]([CH3:29])[O:26][C@@H:27]([CH3:28])[C@@H:21]1[C:12]1([C:17](=[O:18])[NH:16][C:15](=[O:19])[NH:14][C:13]1=[O:20])[CH2:11]2>O1CCCC1.O>[F:5][C:6]1[C:7]2[O:32][N:31]=[C:30]([N:33]3[CH:37]=[C:36]([CH2:38][OH:39])[CH:35]=[N:34]3)[C:8]=2[CH:9]=[C:10]2[C:23]=1[N:22]1[CH2:24][C@@H:25]([CH3:29])[O:26][C@@H:27]([CH3:28])[C@@H:21]1[C:12]1([C:17](=[O:18])[NH:16][C:15](=[O:19])[NH:14][C:13]1=[O:20])[CH2:11]2

Participants

6

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 67433760HCID 67433760, compound

Product 1

HCID 67432359HCID 67432359, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (0.434 mL, 0.87 mmol) was added to an ice cooled solution of methanol (0.035 mL, 0.87 mmol) in tetrahydrofuran (10 mL). The solution was warmed to room temp and stirred for 1 hour. 1.5 ml of this solution was added to a solution of ethyl 1-[(2R,4S,4aS)-11-fluoro-2,4-dimethyl-2′,4′,6′-trioxo-1,1′,2,3′,4,4′,4a,6′-octahydro-2′H,6H-spiro[1,4-oxazino[4,3-a][1,2]oxazolo[4,5-g]quinoline-5,5′-pyrimidin]-8-yl]-1H-pyrazole-4-carboxylate (Example 37, 60 mg, 0.11 mmol). The reaction was stirred at room temp for 12 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic layers were washed twice with brine, dried over MgSO4 and concentrated. The residue was purified by reverse phase HPLC to give product as a solid. Yield: 20 mg.

Workup

  1. stirringThe reaction was stirred at room temp for 12 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layers were washed twice with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by reverse phase HPLC
  7. customto give product as a solid

Sources & evidence

ORD record
ord-9dacd77eca7749509ab8e0d532544d7b
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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