Sodium Thiosulfate → HCID 178437011, compound

HRID 1962869Notes

Reaction equation

HRID 1962869 reaction equation
[C:1]([SiH2:5][O:6][C:7]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:8]([NH:12][C:13](=[O:30])[CH:14]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][C:22]([C:28]#[CH:29])=[CH:21]2)[S:15][CH3:16])([CH3:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]([SiH2:5][O:6][C:7]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:8]([NH:12][C:13](=[O:30])[CH:14]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][C:22]([C:28]#[CH:29])=[CH:21]2)[S:15][CH3:16])([CH3:11])[CH:9]=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178437012HCID 178437012, compound

Product 1

HCID 178437011HCID 178437011, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-1-methyl-ethyl]-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (1.90 g) from Stage 2 above in dichloromethane (55 ml) was treated with Dess-Martin periodinane (1.615 g). The reaction mixture was stirred at room temperature for 1 h30 and then treated with saturated aqueous NaHCO3 and saturated aqueous sodium thiosulphate. The organic layer was washed thrice with saturated aqueous NaHCO3. The organic phase was separated, dried over sodium sulphate, filtered and evaporated to yield 1.694 g of N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-2-oxo-ethyl]-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide which was used as such in Stage 4 described below.

Workup

  1. washThe organic layer was washed thrice with saturated aqueous NaHCO3
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0312e05d50dc4e0eb684f91b5f543f74
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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