Sodium Thiosulfate → HCID 86628372, compound

HRID 553282Notes

Reaction equation

HRID 553282 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][OH:25])=[CH:19][CH:18]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].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+]>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]=[O:25])=[CH:19][CH:18]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67165102HCID 67165102, compound

Product 1

HCID 86628372HCID 86628372, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

[4-(2-Hydroxyethyl)benzyl]-(2-phenylethyl)carbamic acid tert-butyl ester (238 mg) in dichloromethane (10 mL) was treated with Dess-Martin periodinane (341 mg) and stirred for 1 hour. The reaction mixture was added to a mixture of ethyl acetate (10 mL), saturated aqueous sodium thiosulphate solution (10 mL) and saturated aqueous sodium bicarbonate (10 mL), and the mixture was stirred vigorously for 10 minutes. The phases were separated. The aqueous layer was extracted with ethyl acetate and the combined organics were washed with water, dried (magnesium sulfate) and evaporated to give the subtitle compound as an oil (232 mg).

Workup

  1. stirringthe mixture was stirred vigorously for 10 minutes
  2. customThe phases were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organics were washed with water
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-2970460d7bee46a2b4f86c10c5a7e60d
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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