(Bis(2-methoxyethyl)amino)sulfur trifluoride → Ethyl [4-(1-fluoro-2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)-2-methylphenoxy]acetate

HRID 460032Notes

Reaction equation

HRID 460032 reaction equation
COCCN(S(F)(F)[F:11])CCOC.O[CH:15]([C:33]1[CH:45]=[CH:44][C:36]([O:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[C:35]([CH3:46])[CH:34]=1)[CH2:16][C:17]1[S:21][C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[N:19][C:18]=1[CH3:32]>ClCCl>[F:11][CH:15]([C:33]1[CH:45]=[CH:44][C:36]([O:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[C:35]([CH3:46])[CH:34]=1)[CH2:16][C:17]1[S:21][C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[N:19][C:18]=1[CH3:32]

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 17972190Ethyl [4-(1-hydroxy-2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)-2-methylphenoxy]acetate2×

Product 1

HCID 17972193Ethyl [4-(1-fluoro-2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)-2-methylphenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of bis-(2-methoxyethyl)aminosulfur trifluoride (0.031 g) in anhydrous dichloromethane (0.05 ml) at −78° C. under nitrogen was added a solution of ethyl [4-(1-hydroxy-2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)-2-methylphenoxy]acetate (intermediate 16, 0.061 g) in anhydrous dichloromethane (1 ml). After two hours at −78° C. the reaction was quenched with saturated sodium bicarbonate solution (2.5 ml) and the product extracted into dichloromethane. The organic extract was separated by hydrophobic frit and evaporated to yield a yellow oil. Purification by flash column chromatography using neat cyclohexane and ethyl acetate:cyclohexane (1:9) as eluents to give the title compound as a yellow solid.

Workup

  1. customAfter two hours at −78° C. the reaction was quenched with saturated sodium bicarbonate solution (2.5 ml)
  2. extractionthe product extracted into dichloromethane
  3. extractionThe organic extract
  4. customwas separated by hydrophobic frit
  5. customevaporated
  6. customto yield a yellow oil
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-981be8e6dd3c4bbf9d973fc1d6fc795a
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

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