Allyl bromide → (r)-n-Allyl-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-n-(thiazol-2-yl)benzenesulfonamide

HRID 1876727Notes

Reaction equation

HRID 1876727 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]3[S:18][CH:19]=[CH:20][N:21]=3)(=[O:15])=[O:14])=[CH:9][CH:8]=2)[C:3]1=[O:22].[CH:23](N(CC)C(C)C)([CH3:25])[CH3:24].C(Br)C=C>C(Cl)Cl>[CH2:25]([N:16]([C:17]1[S:18][CH:19]=[CH:20][N:21]=1)[S:13]([C:10]1[CH:11]=[CH:12][C:7]([N:4]2[CH2:5][CH2:6][C@@H:2]([OH:1])[C:3]2=[O:22])=[CH:8][CH:9]=1)(=[O:14])=[O:15])[CH:23]=[CH2:24]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 59466118(R)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

Product 1

HCID 59465667(r)-n-Allyl-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-n-(thiazol-2-yl)benzenesulfonamideYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesised according to general procedure 67. To a stirring suspension of (R)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (200 mg, 0.59 mmol) in CH2Cl2 (0.50 mL), under N2, at 0° C., was added N,N-diisopropylethylamine (0.10 mL, 0.59 mmol) followed by allylbromide (51 uL, 0.59 mmol). The mixture was stirred at ambient temperature for 19 hours. The mixture was evaporated to dryness under reduced pressure. The residue was purified via silica gel using 50% EtOAc in hexanes to give the desired sulfonamide as a white solid (220 mg, 0.57 mmol, 96% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.86-7.80 (m, 4H), 7.37 (d, J=4.7 Hz, 1H), 6.93 (d, J=4.7 Hz, 1H), 5.92-5.83 (m, 2H), 5.17 (dd, J=1.3, 10.3 Hz, 1H), 4.98 (q, J=1.4 Hz, 1H), 4.55 (dt, J=5.3, 1.7 Hz, 2H), 4.36-4.30 (m, 1H), 3.81-3.76 (m, 1H), 3.70 (td, J=9.5, 5.4 Hz, 1H), 2.45-2.38 (m, 1H), 1.90-1.80 (m, 1H).

Workup

  1. customSynthesised
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. customThe residue was purified via silica gel using 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-3b0efb4eed2547f3a707de2878dac9fa
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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