Sodium Thiosulfate → 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-methyl-2-oxo-1-prop-2-ynyloxymethyl-ethyl)-2-methylsulfanyl acetamide

HRID 1962877Notes

Reaction equation

HRID 1962877 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:27][CH3:28])[C:15]([NH:17][C:18]([CH3:26])([CH2:21][O:22][CH2:23][C:24]#[CH:25])[CH2:19][OH:20])=[O:16])=[CH:8][CH:7]=2)#[CH: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]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:27][CH3:28])[C:15]([NH:17][C:18]([CH3:26])([CH2:21][O:22][CH2:23][C:24]#[CH:25])[CH:19]=[O:20])=[O:16])=[CH:8][CH:7]=2)#[CH:2]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 595654102-(3-ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methyl-1-prop-2-ynyloxymethyl-ethyl)-2-methylsulfanyl-acetamide

Product 1

HCID 595653162-(3-ethynyl-quinolin-6-yloxy)-N-(1-methyl-2-oxo-1-prop-2-ynyloxymethyl-ethyl)-2-methylsulfanyl acetamideYield 110.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methyl-1-prop-2-ynyloxymethyl-ethyl)-2-methylsulfanyl-acetamide (1.0 g) from Stage 3 above in dichloromethane (40 ml) was treated with Dess-Martin periodinane (1.277 g). The reaction mixture was stirred at room temperature for 2.5 and then treated with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate. The organic layer was washed with sat. aqueous NaHCO3. After separation, the organic phase was dried over sodium sulphate, filtered and evaporated to yield 1.10 g of 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-methyl-2-oxo-1-prop-2-ynyloxymethyl-ethyl)-2-methylsulfanyl acetamide as a crude product which was used in the next step (Stage 5, described below) without any further purification. 1H NMR (CDCl3) δ ppm: [{9.51 (s), 9.49 (s) 1H}, isomer A and isomer B]; 8.86 (1H, d); 8.22 (1H, d); 8.07 (1H, d); 7.53-7.50 (1H, m); [{7.58 (s br), 7.48 (s br) 1H}, isomer A and isomer B]; 7.26 (1H, m); 5.72 (1H, s); 4.16-3.87 (4H, m); 3.28 (1H, s); 2.48 (1H, m); [{2.22 (s), 2.20 (s) 3H}, isomer A and isomer B]; 1.52 (3H, s).

Workup

  1. washThe organic layer was washed with sat. aqueous NaHCO3
  2. customAfter separation
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7e5b5a1853574ee7b8eda6648cba9a0b
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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