Water → HCID 90295830, compound

HRID 1050200Notes

Reaction equation

HRID 1050200 reaction equation
[O:1]=[C:2]1[N:6]2[C:7]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][C:16]4=[O:21])=[CH:11][C:8]=3[O:9][CH2:10][C@H:5]2[C@@H:4]([CH2:22]CS([O-])(=O)=O)[O:3]1.[K].[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.C(Cl)Cl.CO.O>CN(C=O)C>[O:1]=[C:2]1[N:6]2[C:7]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][C:16]4=[O:21])=[CH:11][C:8]=3[O:9][CH2:10][C@H:5]2[C@H:4]([CH2:22][N:33]2[C:29](=[O:39])[C:30]3[C:31](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:32]2=[O:34])[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 21226129Dichloromethane methanolHCID 24194345Phthalimide potassium saltHCID 131736049HCID 131736049, compound2×

Product 1

HCID 90295830HCID 90295830, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound ((3R,3aS)-1-oxo-7-(3-oxomorpholin-4-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methylmethanesulfonate (3.91 g, 9.81 mmol) prepared as above in (c) was dissolved in 50 ml of DMF. Phthalimide potassium (2.72 g, 14.72 mmol) was added and the mixture was allowed to react at 80° C. for 2 h. TLC (DCM/MeOH=10/1) was employed to monitor the reaction. After the reaction completed, water (80 ml) was added for dilution. There was white solid precipitated, which was filtered and dried. The filtrate was extracted with EA (50 ml×3). The organic phase was combined, and washed sequentially with water (30 ml) and saturated NaCl (30 ml) solution, dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated to afford totally 3.71 g of white solid, yield: 84.2%.

Workup

  1. customto react at 80° C. for 2 h
  2. customthe reaction
  3. customprecipitated
  4. filtrationwhich was filtered
  5. customdried
  6. extractionThe filtrate was extracted with EA (50 ml×3)
  7. washwashed sequentially with water (30 ml) and saturated NaCl (30 ml) solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-17acac5298e64c52b92fedf69d40c0b4
Source dataset
uspto-grants-2016_07
Patent number
US09382265B2

Reaction notes

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