Tetrahydrofuran → HCID 14856359, compound

HRID 1089548Notes

Reaction equation

HRID 1089548 reaction equation
O1CCCC1.[CH3:6][S:7]([NH:10][C:11]1[CH:23]=[CH:22][C:14]2[O:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][O:21][C:13]=2[CH:12]=1)(=[O:9])=[O:8].[CH3:24][S:25]([NH:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)(=[O:27])=[O:26]>N1C=CC=CC=1>[CH3:6][S:7]([NH:10][C:11]1[CH:23]=[CH:22][C:14]2[O:15][CH2:16][CH2:17][N:18]([C:33](=[O:34])[C:32]3[CH:36]=[CH:37][C:29]([NH:28][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:30][CH:31]=3)[CH2:19][CH2:20][O:21][C:13]=2[CH:12]=1)(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 117911194-[(Methylsulfonyl)amino]benzoyl chlorideHCID 14856361HCID 14856361, compound

Product 1

HCID 14856359HCID 14856359, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To tetrahydrofuran add 9-[(methylsulfonyl)amino]-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine, pyridine, and 4-[(methylsulfonyl)amino]benzoyl chloride. Monitor the progress of the reaction by thin-layer chromatography. Upon completion, remove the solvent in vacuo. Partition the residue between aqueous NaHCO3 and EtOAc. Separate the layers and wash the organic layer with 1M aqueous HCl. Separate and dry (Na2SO4) the organic layer. Remove the solvent in vacuo to obtain the title compound.

Workup

  1. customMonitor the progress of the reaction by thin-layer chromatography
  2. customUpon completion, remove the solvent in vacuo
  3. customPartition the residue between aqueous NaHCO3 and EtOAc
  4. customSeparate the layers
  5. washwash the organic layer with 1M aqueous HCl
  6. customSeparate
  7. dry with materialdry (Na2SO4) the organic layer
  8. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-26e0651da25241ccbaa57d73565ce763
Source dataset
uspto-grants-1990_10
Patent number
US04966967

Reaction notes

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