Dimethylformamide → HCID 90370335, compound

HRID 2176024Notes

Reaction equation

HRID 2176024 reaction equation
[CH3:1][C:2]([CH3:37])([CH2:6][CH2:7][C:8](=[O:36])[N:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[O:23][C:24](=[O:35])[C:25]3[C:30]4[CH2:31][CH2:32][CH2:33][CH2:34][C:29]=4[S:28][C:26]=3[N:27]=2)[CH:17]=1)[CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:3]([OH:5])=[O:4].[CH3:38]N(C=O)C.CI.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:37][C:2]([CH3:1])([CH2:6][CH2:7][C:8](=[O:36])[N:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[O:23][C:24](=[O:35])[C:25]3[C:30]4[CH2:31][CH2:32][CH2:33][CH2:34][C:29]=4[S:28][C:26]=3[N:27]=2)[CH:17]=1)[CH:10]([CH2:11][CH3:12])[CH2:13][CH3:14])[C:3]([O:5][CH3:38])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 90370149HCID 90370149, compound

Product 1

HCID 90370335HCID 90370335, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4.81 g of 2,2-dimethyl-5-oxo-5-{[3-(4-oxo-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-2-yl)benzyl](pentan-3-yl)amino}pentanoic acid and 50 mL of DMF were added 2.59 g of methyl iodide and 3.16 g of potassium carbonate, followed by stirring for 1 hour at room temperature. Water was added to a reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was recrystallized from ethanol, thereby obtaining 3.24 g of methyl 2,2-dimethyl-5-oxo-5-{[3-(4-oxo-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-2-yl)benzyl](pentan-3-yl)amino}pentanoate as a yellowish white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e9e46324934e413a8c13f625172609a2
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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