Sodium Thiosulfate → HCID 131726979, compound

HRID 751473Notes

Reaction equation

HRID 751473 reaction equation
[CH3:1][CH:2]([CH2:36][CH3:37])[C@H:3]([NH:24][C:25]([C:27]1[O:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[CH:31]=1)=[O:26])[C:4](=[O:23])[NH:5][CH:6]1[CH2:12][CH2:11][CH2:10][N:9]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:15])=[O:14])[CH2:8][CH:7]1[OH:22].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][CH:2]([CH2:36][CH3:37])[C@H:3]([NH:24][C:25]([C:27]1[O:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[CH:31]=1)=[O:26])[C:4](=[O:23])[NH:5][CH:6]1[CH2:12][CH2:11][CH2:10][N:9]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:14])=[O:15])[CH2:8][C:7]1=[O:22]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 131726980HCID 131726980, compound

Product 1

HCID 131726979HCID 131726979, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of the compound of example 193 (37 mg, 0.07 mmol) in CH2Cl2 (0.5 ml) was added Dess-Martin reagent (45 mg, 0.105 mmol). After stirring for 30 minutes, solutions of sodium thiosulfate (10% in water, 0.50 ml) and saturated aqueous sodium bicarbonate (0.50 ml) were added simultaneously to the reaction. The mixture was then extracted with dichloromethane (2 times). The organic layer was dried, filtered, and concentrated. The residue was purified by HPLC to yield the two diastereomers of the title compound as solids (first eluting: 7 mg, second eluting: 5.5 mg): MS (ESI) 526.91 (M+H)+.

Workup

  1. extractionThe mixture was then extracted with dichloromethane (2 times)
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-6e7d7a154c4144d7808215166a94d5d9
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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