Sodium Thiosulfate → HCID 69413326, compound

HRID 1351313Notes

Reaction equation

HRID 1351313 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1[S:9][C:10]([CH:31]=[O:32])=[CH:11][C:12]=1[S:13](=[O:30])(=[O:29])[N:14]([CH2:16][CH:17]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[O:18][CH2:19][O:20][CH3:21])[CH3:15])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)[C:44]2C=CC=[CH:40][C:39]1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1[S:9][C:10]([C:31](=[O:32])[CH:39]([CH3:40])[CH3:44])=[CH:11][C:12]=1[S:13](=[O:30])(=[O:29])[N:14]([CH2:16][CH:17]([C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)[O:18][CH2:19][O:20][CH3:21])[CH3:15])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86600999HCID 86600999, compound

Product 1

HCID 69413326HCID 69413326, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using (3-{[2-(4-fluorophenyl)-2-methoxymethoxyethyl]methylsulfamoyl}-5-formylthiophene-2-yl)carbamic acid t-butyl ester (200 mg), isopropyl group was introduced in the same way as Preparation Example 87, and a crude alcohol was obtained. Dess-Martin reagent (204 mg) was added to a solution of this compound in dichloromethane (2 mL). After stirring for 1 hour, an aqueous solution of saturated sodium bicarbonate and an aqueous solution of sodium thiosulfate were added, and the solution was extracted with ethyl acetate. After washing with saturated sodium chloride water, the solution was dried with anhydrous sodium sulfate. The solution was filtered through a small amount of silica gel, and the title compound (180 mg) was obtained as an orange oily substance.

Workup

  1. additionwas introduced in the same way as Preparation Example 87
  2. customa crude alcohol was obtained
  3. extractionthe solution was extracted with ethyl acetate
  4. washAfter washing with saturated sodium chloride water
  5. dry with materialthe solution was dried with anhydrous sodium sulfate
  6. filtrationThe solution was filtered through a small amount of silica gel

Sources & evidence

ORD record
ord-98a365ad6c784803882b3b8fce6a338d
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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