Pyridine → HCID 67440074, compound

HRID 1665006Notes

Reaction equation

HRID 1665006 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10].N1C=CC=CC=1.[CH2:21]([O:23][C:24](=[O:34])[CH2:25][NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:22]>ClCCl>[CH2:21]([O:23][C:24](=[O:34])[CH2:25][N:26]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[S:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:14])([F:13])[F:1])(=[O:11])=[O:10])[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 80908N-Benzylglycine ethyl esterHCID 1366162-Trifluoromethylbenzenesulphonyl chloride

Product 1

HCID 67440074HCID 67440074, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-trifluoromethylbenzenesulfonyl chloride (3.8 g) in dichloromethane (100 mL) under argon was added pyridine (14 mL). A solution of N-benzylglycine ethylester (2 g) in dichloromethane (40 mL) was added slowly. The mixture was stirred at r.t. overnight and then concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with water. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane to cyclohexane/ethyl acetate 1:1) to give [benzyl-(2-trifluoromethyl-benzenesulfonyl)-amino]-acetic acid ethyl ester (2.61 g) as a colorless oil. MS: 402.1 ([M+H]+)

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe product was purified by chromatography (SiO2, cyclohexane to cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-47240197dbca412a9585928b710ef906
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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