4-Iodobenzenesulfonyl chloride → HCID 58619004, compound
Reaction equation
[N:1]([C@@H:4]([CH:12]1[CH2:16][CH2:15][NH:14][CH2:13]1)[C:5]([N:7]1[CH2:11][CH2:10][S:9][CH2:8]1)=[O:6])=[N+]=[N-].C(NC(C)C)(C)C.[I:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl>[I:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([N:14]2[CH2:15][CH2:16][CH:12]([C@H:4]([NH2:1])[C:5](=[O:6])[N:7]3[CH2:11][CH2:10][S:9][CH2:8]3)[CH2:13]2)(=[O:33])=[O:32])=[CH:27][CH:26]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 28 mg (0.1 mmol) of 3-[(2S)-2-azido-2-pyrrolidin-3-ylethanoyl]-1,3-thiazolidine in methylene chloride (1 mL) was added 0.030 mL of diisopropylamine and 29 mg (0.12 mmol ) of 4-iodobenzenesulfonyl chloride. The mixture was stirred for 18 h and subjected directly to preparative TLC on silica gel (eluent: 60% ethyl acetate in hexanes) to give the desired sulfonamide (40 mg) as an off white solid. This solid was dissolved in wet THF (10%) and 25 mg (0.1 mmol) of triphenyl phosphine was added and stirred at 60° C. for 5 h and concentrated. A mixture of diastereomers were separated by preparative TLC on silca gel (10% methanol in CH2Cl2). Diastereomer I (faster moving isomer) 1H NMR (500 MHz, CDCl3) δ 7.9 (d, 2H, J=8.1 Hz), 7.52 (d, 2H, J=8.1 Hz), 4.65–4.47 (m, 2H), 3.86 (m, 1H), 3.78 9 (dd, 1H, J=6 and 8 Hz), 3.43 (m, 1H), 3.25–3.02 (m, 4H), 2.4 (m, 1H), 1.95 (m, 2H). Diastereomer II (slower moving isomer) 1H NMR (500 MHz, CDCl3) δ 7.91 (d, 2H, J=8.2 Hz), 7.56 (d, 2H, J=8.2 Hz), 4.63–4.41 (m, 2H), 3.86 (m, 1H), 3.79 (m, 0.5H), 3.64 (m, 0.5H), 3.37 (m, 3H), 3.25 (dd, 1H, J=10 and 14 Hz), 3.12 (m, 2H), 3.01 (t, 1H, J=4.4 Hz), 2.4 (m, 1H), 1.94 (m, 1H), 1.61 (m, 1H).
Sources & evidence
- ORD record
- ord-7e37c93f2a774f188465ec5f48523284
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07026316B2
Reaction notes
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