Methanesulfonyl chloride → HCID 66844975, compound

HRID 219040Notes

Reaction equation

HRID 219040 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][C@@H:18]([C:20]2[CH:31]=[CH:30][C:23]3[O:24][C:25]([CH3:29])([CH3:28])[O:26][CH2:27][C:22]=3[CH:21]=2)[O:17][C:16]1=[O:32].[CH3:36][S:37](Cl)(=[O:39])=[O:38]>N1C=CC=CC=1>[CH3:28][C:25]1([CH3:29])[O:24][C:23]2[CH:30]=[CH:31][C:20]([C@H:18]3[O:17][C:16](=[O:32])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][C:4]4[CH:3]=[C:2]([NH:1][S:37]([CH3:36])(=[O:39])=[O:38])[CH:35]=[CH:34][CH:33]=4)[CH2:19]3)=[CH:21][C:22]=2[CH2:27][O:26]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66845744HCID 66845744, compound

Product 1

HCID 66844975HCID 66844975, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (5R)-3-(5-{2-[(3-aminobenzyl)oxy]ethoxy}pentyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (52 mg) in pyridine (4 ml) was treated with methanesulfonyl chloride (13 mg) at 20° C. for 3 h. The mixture was quenched with sat. aqueous sodium bicarbonate (20 ml) and partitioned with DCM. The organic layer was dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified using SPE eluting with DCM then EtOAc-PE (3:1). The selected fractions were evaporated in vacuo to yield the title compound (39 mg).

Workup

  1. customThe mixture was quenched with sat. aqueous sodium bicarbonate (20 ml)
  2. custompartitioned with DCM
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified
  6. washeluting with DCM
  7. customThe selected fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-7c07dd4160fc473d8779c655cd281f6a
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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