Methanesulfonyl chloride → HCID 136358673, compound
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:43]([CH2:44][CH2:45][CH3:46])=[C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[C:26]([S:28]([N:31]4[CH2:36][CH2:35][N:34]([CH2:37][CH3:38])[CH2:33][CH2:32]4)(=[O:30])=[O:29])[CH:25]=[CH:24][C:23]=3[O:39][CH2:40][CH2:41][CH3:42])[NH:19][C:20](=[O:21])[C:15]2=[N:14]1>N1C=CC=CC=1>[CH2:37]([N:34]1[CH2:35][CH2:36][N:31]([S:28]([C:26]2[CH:25]=[CH:24][C:23]([O:39][CH2:40][CH2:41][CH3:42])=[C:22]([C:18]3[NH:19][C:20](=[O:21])[C:15]4[C:16](=[C:43]([CH2:44][CH2:45][CH3:46])[N:13]([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=5[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[N:14]=4)[N:17]=3)[CH:27]=2)(=[O:30])=[O:29])[CH2:32][CH2:33]1)[CH3:38]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Methanesulphonyl chloride (0.156 ml, 2.0 mmol) was added to a stirred solution of the title compound of Example 116 (583 mg, 1.0 mmol) in pyridine (8 ml), under nitrogen, and the resulting solution stirred at 50° C. for 18 hours, then evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water, then the separated organic phase washed with brine, dried (MgSO4) and evaporated under reduced pressure. The resulting brown foam was purified by column chromatography on silica gel, using an elution gradient of dichloromethane:methanol (100:0 to 99:1 to 98:2 to 97:3), to yield the title compound (32%) as a cream foam. Found: C, 53.96; H, 6.01; N, 14.38. C30H39N7O6S2; 0.60 H2O requires C, 53.89; H, 6.06; N, 14.67%. δ (CDCl3): 0.91 (3H, t), 1.01 (3H, t), 1.19 (3H, t), 1.75 (2H, m), 2.07 (2H, m), 2.40 (2H, q), 2.53 (4H, m), 2.93 (2H, t), 3.07 (3H, s), 3.09 (4H, m), 4.29 (2H, t), 7.16 (2H, m), 7.35 (2H, m), 7.57 (1H, t), 7.82 (2H, d), 8.80 (1H, s), 10.74 (1H, s). LRMS: m/z 658 (M+1)+.