4-Methoxybenzenesulfonyl chloride → HCID 19705455, compound

HRID 727568Notes

Reaction equation

HRID 727568 reaction equation
[NH2:1][CH2:2][CH:3]([C:11]1([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]1=[O:24])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(N(C(C)C)CC)(C)C.[CH3:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([S:46](Cl)(=[O:48])=[O:47])=[CH:42][CH:41]=1>C(Cl)Cl>[CH3:38][O:39][C:40]1[CH:41]=[CH:42][C:43]([S:46]([NH:1][CH2:2][CH:3]([C:11]2([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12]2=[O:24])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])(=[O:48])=[O:47])=[CH:44][CH:45]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 19705458HCID 19705458, compound

Product 1

HCID 19705455HCID 19705455, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A cold (0° C.) solution of tert-butyl α-(1-aminomethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (337 mg, 0.867 mmol) in dry CH2Cl2 (3 mL) is treated with diisopropylethylamine (240 μL, 1.30 mmol) and 4-methoxybenzenesulfonyl chloride (215 mg, 1.30 mmol). The solution was allowed to slowly warm to room temperature, stirring overnight under N2. After diluting with CH2Cl2 (25 mL), the solution is washed with dilute NaHCO3 (10 mL), H2O (10 mL), and brine (10 mL). The organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give 460 mg of a yellow oil. The oil was purified by silica gel chromatography (20 g SG; 25% EtOAc/hexane) to provide 383 mg (79%) of the desired material as a white amorphous solid:

Workup

  1. washthe solution is washed with dilute NaHCO3 (10 mL), H2O (10 mL), and brine (10 mL)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2cc4c3bb525e472084bfdaa240ccc1b0
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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