HCID 20786486, compound → HCID 20786344, compound

HRID 1593235Notes

Reaction equation

HRID 1593235 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[C:26]([CH3:27])=[CH:25][C:16]([O:17][CH2:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])=[CH:15][C:14]=2[CH3:28])(=[O:12])=[O:11])=[C:5]([N+:29]([O-:31])=[O:30])[CH:4]=1.[C:32]1([CH3:44])[CH:37]=[CH:36][C:35]([S:38]([CH:41](O)[CH3:42])(=[O:40])=[O:39])=[CH:34][CH:33]=1>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[C:14]([CH3:28])=[CH:15][C:16]([O:17][CH2:18][C:19]([CH3:24])([CH3:23])[C:20]([O:22][CH2:42][CH2:41][S:38]([C:35]3[CH:36]=[CH:37][C:32]([CH3:44])=[CH:33][CH:34]=3)(=[O:40])=[O:39])=[O:21])=[CH:25][C:26]=2[CH3:27])(=[O:12])=[O:11])=[C:5]([N+:29]([O-:31])=[O:30])[CH:4]=1

Participants

4

Reactant 2

HCID 20786486HCID 20786486, compoundHCID 224793001-(4-Methylbenzene-1-sulfonyl)ethan-1-ol

Product 1

HCID 20786344HCID 20786344, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
36 °C

Procedure

A mixture of 3-{4-[4-methoxy-2-nitrophenylaminosulfonyl}-3,5-dimethylphenoxy]-2,2-dimethylpropionic acid (Intermediate A10, 24.2 g, 0.054 mol) and carbonyldiiuidazole (9.5 g, 0.059 mol) was diluted with 45 mL dichloromethane and warmed in a 36° C. bath for 15 min. Then, 4-tolylsulfonylethanol was added, the bath temperature was raised to 55° C., and the solvent was blown off in a nitrogen stream. After 1.5 hr, the stream was stopped, and after 2.5 hr, the cooled reaction mixture was partitioned between ethyl acetate and 1.2 M hydrochloric acid. The aqueous layer was extracted with additional ethyl acetate, and the combined organic layers were washed with water and saturated sodium chloride, concentrated at aspirator pressure and high vacuum. The product, title compound, (34 g, 99%) was carried on without further purification.

Workup

  1. temperaturethe bath temperature was raised to 55° C.
  2. waitafter 2.5 hr
  3. customthe cooled reaction mixture
  4. customwas partitioned between ethyl acetate and 1.2 M hydrochloric acid
  5. extractionThe aqueous layer was extracted with additional ethyl acetate
  6. washthe combined organic layers were washed with water and saturated sodium chloride
  7. concentrationconcentrated at aspirator pressure and high vacuum
  8. customThe product, title compound, (34 g, 99%) was carried on without further purification

Sources & evidence

ORD record
ord-654d4c77f46a403b86a489941aabb8c9
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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