Methanesulfonic Acid → HCID 86590437, compound

HRID 1990925Notes

Reaction equation

HRID 1990925 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[NH:40][C:22]4[N:23]=[C:24]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[N:25]=[C:26]([NH:27][CH2:28][CH2:29][NH:30][C:31](=[O:33])[CH3:32])[C:21]=4[CH:20]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[CH3:41][S:42]([OH:45])(=[O:44])=[O:43]>CO.C1COCC1>[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][N:14]([C:17]([C:19]3[NH:40][C:22]4[N:23]=[C:24]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)[N:25]=[C:26]([NH:27][CH2:28][CH2:29][NH:30][C:31](=[O:33])[CH3:32])[C:21]=4[CH:20]=3)=[O:18])[CH2:15][CH2:16]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 10218428HCID 10218428, compound

Product 1

HCID 86590437HCID 86590437, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 26.135 (5.37 g, 9.59 mmol) is dissolved in a mixture of methanol (50 mL) and THF (100 mL), and methanesulfonic acid (921 mg, 9.59 mmol) is added dropwise. The solution is allowed to stand for 15 minutes and then concentrated in vacuo. The pale yellow foam is dissolved in ethanol and concentrated to give 6.3 g (100%) of a pale yellow amorphous solid, mp. 150-156° C. 1H NMR (400 MHz, DMSO-D6): δ=1.79 (s, 3H), 1.96 (m, 2H), 2.30 (s, 3H), 2.64 (t, 2H, J=7.2 Hz), 3.12 (m, 4H), 3.35 (m, 6H), 3.50-3.70 (m, 4H), 4.46 (d, 2H, J=6.8 Hz), 7.02 (s, 1H), 7.26 (d, 2H, J=8.4 Hz), 7.36 (d, 2H, J=8.4 Hz), 7.40-7.48 (m, 3H), 7.87 (brs, 1H), 8.04 (brs, 1H), 8.39 (dd, 2H, J=2.0, 7.2 Hz), 9.68 (brs, 1H), 12.09 (brs, 1H). MS (ES): 560.0/562.0 (100/33) [MH+]. tR (method B)=10.5 min.

Workup

  1. additionis added dropwise
  2. concentrationconcentrated in vacuo
  3. dissolutionThe pale yellow foam is dissolved in ethanol
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cae35b4480694805abf00db79ac1c554
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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