Hydrochloric Acid → 1-[(4-Methoxyphenyl)sulfonyl]-D-proline

HRID 1954082Notes

Reaction equation

HRID 1954082 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.Cl>O.O1CCOCC1.CN(C)C1C=CN=CC=1>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([N:1]2[CH2:8][CH2:7][CH2:6][C@@H:2]2[C:3]([OH:5])=[O:4])(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 8988D-Proline

Product 1

HCID 7449021-[(4-Methoxyphenyl)sulfonyl]-D-proline

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

D-proline (15 g, 130.3 mmol) is dissolved in a 1:1 mixture of water (150 mL) and p-dioxane (150 mL) and then triethyl amine (40 mL, 287 mmol), 4-methoxyphenylsulfonyl chloride (29.0 g, 140.3 mmol), and the 4-dimethylaminopyridine (1.5 g, 13.0 mmol) are added. The solution is stirred at room temperature overnight. The reaction mixture is then treated with 1N HCl until the solution is acidic (pH=2). The resulting solution is extracted three times with ethyl acetate. The ethyl acetate layers are washed with ammonium chloride, dried (MgSO4), filtered and evaporated to give the crude compound. Cl+ MS: m/z (rel intensity) (M+ +H 286, 100 ).

Workup

  1. extractionThe resulting solution is extracted three times with ethyl acetate
  2. washThe ethyl acetate layers are washed with ammonium chloride
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7143f145fb5445aa84726d366d060aec
Source dataset
uspto-grants-2000_09
Patent number
US06121272

Reaction notes

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