Sodium Thiosulfate → HCID 86628376, compound

HRID 553311Notes

Reaction equation

HRID 553311 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][OH:26])[CH:19]=1)[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=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:27])[N:7]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH:25]=[O:26])[CH:19]=1)[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67165738HCID 67165738, compound

Product 1

HCID 86628376HCID 86628376, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [3-(2-hydroxy-ethyl)-benzyl]-(3-pyridin-2-yl-propyl)-carbamic acid tert-butyl ester (90 mg) in anhydrous dichloromethane (8 mL) under nitrogen was treated with Dess-Martin periodinane (123 mg) and the mixture stirred for 90 minutes. Ethyl acetate (8 mL) was added followed by saturated aqueous sodium thiosulphate (8 mL) and saturated aqueous sodium bicarbonate (8 mL), the resultant mixture was stirred vigorously for 10 minutes before being extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium bicarbonate, dried and the solvent removed under reduced pressure to yield the sub-titled compound (90 mg).

Workup

  1. extractionbefore being extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium bicarbonate
  4. customdried
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-31badbc9b6ea4682b7d420941b7df5e0
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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