Methanesulfonic Acid → HCID 178505362, compound

HRID 406905Notes

Reaction equation

HRID 406905 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:23]3[CH2:28][CH2:27][NH:26][CH:25]=[N:24]3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1.[CH3:29][S:30]([OH:33])(=[O:32])=[O:31]>CO.C(Cl)Cl>[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:23]3[CH2:28][CH2:27][NH:26][CH:25]=[N:24]3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178523392HCID 178523392, compound2×

Product 1

HCID 178505362HCID 178505362, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The compound obtained in Example 5 (16.7 g, 39.8 mmol) was suspended in MeOH/CH2Cl2 (1/4 v/v, 350 mL) and stirred at 50 until the compound obtained in Example 5 was dissolved clearly. The mixture thus obtained was cooled to 0 and methylsulfonic acid (2.9 mL, 43.8 mmol, 1.3 eq, Aldrich 471356) was added thereto at 0. The resulting mixture was evaporated in vacuo to remove solvent. The resultant solid was suspended in absolute EtOH (100 mL) and the suspension was stirred at 90 to dissolve solid clearly. The resulting mixture was cooled to 0 and stirred at 0 for 2 hrs. The solid thus produced was filtered off, washed with absolute EtOH (100 mL), and dried under high vacuum to obtain the title compound.

Workup

  1. dissolutionwas dissolved clearly
  2. customThe mixture thus obtained
  3. additionwas added
  4. customThe resulting mixture was evaporated in vacuo
  5. customto remove solvent
  6. dissolutionto dissolve solid clearly
  7. temperatureThe resulting mixture was cooled to 0
  8. stirringstirred at 0 for 2 hrs
  9. customThe solid thus produced
  10. filtrationwas filtered off
  11. washwashed with absolute EtOH (100 mL)
  12. customdried under high vacuum

Sources & evidence

ORD record
ord-378cd59af1704878bed479a05fb3b419
Source dataset
uspto-grants-2014_06
Patent number
US08754210B2

Reaction notes

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