Methanol → HCID 67433538, compound

HRID 245579Notes

Reaction equation

HRID 245579 reaction equation
[BH4-].[Li+].CO.[Li+].[BH4-].CO.[F:9][C:10]1[C:11]2[O:36][N:35]=[C:34]([C:37](OCC)=[O:38])[C:12]=2[CH:13]=[C:14]2[C:27]=1[N:26]1[CH2:28][C@@H:29]([CH3:33])[O:30][C@@H:31]([CH3:32])[C@@H:25]1[C:16]1([C:21](=[O:22])[NH:20][C:19](=[O:23])[NH:18][C:17]1=[O:24])[CH2:15]2>C1COCC1.O>[F:9][C:10]1[C:11]2[O:36][N:35]=[C:34]([CH2:37][OH:38])[C:12]=2[CH:13]=[C:14]2[C:27]=1[N:26]1[CH2:28][C@@H:29]([CH3:33])[O:30][C@@H:31]([CH3:32])[C@@H:25]1[C:16]1([C:17](=[O:24])[NH:18][C:19](=[O:23])[NH:20][C:21]1=[O:22])[CH2:15]2

Participants

7

Reactant 4

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 70901148HCID 70901148, compoundHCID 131731215HCID 131731215, compound

Product 1

HCID 67433538HCID 67433538, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

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 THF (10 ml). The solution was warmed to room temperature and stirred for 1 hour. 1.5 ml of the LiBH4/MeOH solution was added to a solution of (2R,4S,4aS)-rel-ethyl 11-fluoro-2,4-dimethyl-2′,4′,6′-trioxo-2,2′,3′,4,4a,4′,6,6′-octahydro-1H,1′H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5′-pyrimidine]-8-carboxylate (Example 134, 30 mg, 0.07 mmol) in 5 ml of THF. The reaction was stirred at room temperature of 1 hour. The reaction was diluted with water and extracted with ethyl acetate 2×. The organic layers were washed twice with brine, dried over MgSO4 and concentrated. The residue was purified by HPLC (Acetonitrile (5 to 50%)/Water with a TFA modifier over 10 minutes). Freeze dried for 48 hours to give the title compound (22 mg, 0.053 mmol, 81%).

Workup

  1. stirringThe reaction was stirred at room temperature of 1 hour
  2. extractionextracted with ethyl acetate 2×
  3. washThe organic layers were washed twice with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by HPLC (Acetonitrile (5 to 50%)/Water with a TFA modifier over 10 minutes)
  7. customFreeze dried for 48 hours

Sources & evidence

ORD record
ord-824b4abd21df4bc48d7b4e7ef1193ead
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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