2-Naphthalenesulfonyl chloride → HCID 131723839, compound

HRID 1264418Notes

Reaction equation

HRID 1264418 reaction equation
[N:1]1([C:7]([C@H:9]2[NH:13][CH2:12][C@@H:11]([S:14][C:15](=[O:17])[CH3:16])[CH2:10]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[S:28](Cl)(=[O:30])=[O:29].OS([O-])(=O)=O.[K+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[S:28]([N:13]1[C@H:9]([C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])[CH2:10][C@H:11]([S:14][C:15](=[O:17])[CH3:16])[CH2:12]1)(=[O:29])=[O:30]

Participants

6

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 516920Potassium bisulfateHCID 131723840HCID 131723840, compound

Product 1

HCID 131723839HCID 131723839, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

300 mg (1.17 mmol) (3S,5S)-Thioacetic acid S-[5-(piperidine-1-carbonyl)-pyrrolidin-3-yl] ester in 25 ml CH2Cl2 were treated with 398 mg (1.75 mmol, 1.5 eq) 2-naphthalene sulfonylchloride in the presence of 214 mg (1.75 mmol, 1.5 eq) DMAP at RT for 1.5 h. The solution was added to 1M KHSO4, the phases were separated and the inorganic extracted with CH2Cl2, the combined organic phases were washed with 1M KHSO4, water and brine, dried over Na2SO4 and were concentrated. Flash chromatography yielded 280 mg (54%) (3S,5S)-Thioacetic acid S-[1-(naphthalene-2-sulfonyl)-5-(piperidine-1-carbonyl)-pyrrolidin-3-yl] ester as white crystals.

Workup

  1. customthe phases were separated
  2. extractionthe inorganic extracted with CH2Cl2
  3. washthe combined organic phases were washed with 1M KHSO4, water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationwere concentrated

Sources & evidence

ORD record
ord-abe8bfa1751c4a8aa6fef918e81c84ea
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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