Sodium Thiosulfate → HCID 86753810, compound

HRID 1417612Notes

Reaction equation

HRID 1417612 reaction equation
[Si:1]([O:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:34])[C@@H:23]([CH3:33])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:32])([CH3:31])[CH:28]=[CH:29][CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[OH:36].[Na+].ClC1C=CC=C(C(OO)=O)C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Si:1]([O:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:34])[C@@H:23]([CH3:33])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:32])([CH3:31])[C@H:28]5[O:36][C@H:29]5[CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86753808HCID 86753808, compound

Product 1

HCID 86753810HCID 86753810, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound (41b) (40 mg, 0.08 mmol) in 4 ml of dichloromethane was added 15 mg (0.18 mmol) of sodium hydrogen carbonate under ice-cooling. To the resulting suspension was added 25 mg (0.116 mmol) of 80% m-chloroperbenzoic acid, and the mixture stirred for 18.5 hours at room temperature. To the reaction mixture were added 0.5N aqueous sodium thiosulfate solution and an aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a column chromatography (Merck, Lobar column, size A; chloroform:methanol=100:1) to give 28 mg (85%) of Compound (43b).

Workup

  1. temperaturecooling
  2. extractionan aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a column chromatography (Merck, Lobar column, size A

Sources & evidence

ORD record
ord-25348dde7bcc472689c3d930fdac2507
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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