Potassium Carbonate → HCID 86585065, compound

HRID 1264411Notes

Reaction equation

HRID 1264411 reaction equation
[C:1]([S:4][C@H:5]1[CH2:9][N:8]([S:10]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)(=[O:12])=[O:11])[C@H:7]([C:23](O)=[O:24])[CH2:6]1)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH3:32][NH:33][C:34]1[CH:42]=[CH:41][C:37](C(O)=O)=[CH:36][CH:35]=1.[C:43]([O-:46])([O-])=[O:44].[K+].[K+].OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1.C1COCC1>[C:1]([S:4][C@H:5]1[CH2:9][N:8]([S:10]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)(=[O:11])=[O:12])[C@H:7]([C:23]([N:33]([CH3:32])[C:34]2[CH:35]=[CH:36][C:37]([C:43]([OH:46])=[O:44])=[CH:41][CH:42]=2)=[O:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 663454-(Methylamino)benzoic acidHCID 516920Potassium bisulfateHCID 86585063HCID 86585063, compound

Product 1

HCID 86585065HCID 86585065, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 200 mg (0.52 mmol) (2S,4R)-4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid in 10 ml toluene and 4 ml THF were added 226 μl (2.6 mmol, 5eq) oxalyl chloride and the solution was stirred at RT for 2 h, and was concentrated. The residue was dissolved in 8 ml THF, and the solution was added at 0° C. to a suspension of 180 mg (1.19 mmol, 2.2 eq) 4-methylamino benzoic acid and 360 mg (2.6 mmol, 5eq) K2CO3 in 8 ml THF. After 2.5 h the solution was acidified by 1M KHSO4 and extracted with EtOAc, the organic phase was washed with brine and dried over Na2SO4. Column chromatography yielded 91 mg (35%) (2S,4R)-4-[[4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino]-benzoic acid as white solid, MS: 513 (MH+).

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in 8 ml THF
  3. extractionextracted with EtOAc
  4. washthe organic phase was washed with brine
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e17e6148c7c94756b1e1f837ad5db480
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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