p-Toluenesulfonic acid monohydrate → (R)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

HRID 1098687Notes

Reaction equation

HRID 1098687 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]3[S:21][CH:22]=[CH:23][N:24]=3)(=[O:18])=[O:17])=[CH:12][CH:11]=2)[C:4](=O)[O:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[OH:6][C@@H:5]1[CH2:7][CH2:8][N:9]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]3[S:21][CH:22]=[CH:23][N:24]=3)(=[O:18])=[O:17])=[CH:12][CH:11]=2)[C:4]1=[O:3]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59466393(R)-4-[2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethylamino]-N-(thiazol-2-yl)benzene-sulfonamide

Product 1

HCID 59466118(R)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamideYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of (R)-4-[2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethylamino]-N-(thiazol-2-yl)benzene-sulfonamide (833 mg, 2.15 mmol), p-toluenesulfonic acid monohydrate (42 mg, 0.22 mmol), and THF (10 mL) was stirred at 80° C. for 3 hours. The mixture was concentrated to dryness under reduced pressure. The residue was purified by silica gel chromatography (5% MeOH in DCM) to give (R)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzene sulfonamide as a white solid (496 mg, 1.4 mmol, 65% yield). 1H-NMR (400 MHz, DMSO-d6) δ 7.85 (dd, J=2.1, 6.9 Hz, 4H), 7.25 (d, J=4.6 Hz, 1H), 6.82 (d, J=4.6 Hz, 1H), 5.83 (d, J=5.9 Hz, 1H), 4.32 (d, J=5.3 Hz, 1H), 3.77 (dd, J=1.9, 9.0 Hz, 1H), 3.71-3.69 (m, 1H), 2.41-2.38 (m, 1H), 1.84 (dd, J=9.2, 12.3 Hz, 1H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=340.2; tR=0.50 min.

Workup

  1. concentrationThe mixture was concentrated to dryness under reduced pressure
  2. customThe residue was purified by silica gel chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-0dc931e48d204dd19d28e343fa6054b7
Source dataset
uspto-grants-2012_03
Patent number
US08143297B2

Reaction notes

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