Methanesulfonyl chloride → HCID 66844975, compound

HRID 901619Notes

Reaction equation

HRID 901619 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-b3657adc352c42a0bdfb95d7d35806ae
Source dataset
uspto-grants-2008_04
Patent number
US07361787B2

Reaction notes

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