Methanesulfonic Acid → HCID 9847196, compound

HRID 1276188Notes

Reaction equation

HRID 1276188 reaction equation
[C:1]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:8][C:7]=1[NH:17][C:18]([NH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])[CH2:25][CH2:24]1)=[O:19])([O:3]CC)=O.CC(C)([O-])C.[K+].C1COCC1.CS(O)(=O)=O>C(O)C>[CH3:36][O:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[N:26]1[CH2:25][CH2:24][N:23]([CH2:22][CH2:21][N:20]2[C:1](=[O:3])[C:6]3[CH:10]=[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[S:8][C:7]=3[NH:17][C:18]2=[O:19])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 22115541HCID 22115541, compoundHCID 66863523KOtBu THF

Product 1

HCID 9847196HCID 9847196, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 5B (387 mg, 0.762 mmol) in ethanol (5 mL) was treated with 1M potassium t-butoxide/THF (0.84 mL), heated to reflux for 90 minutes, cooled, quenched with 1N HCl(0.84 mL), and partitioned between water and ethyl acetate. The insoluble solid was collected, washed with ethyl acetate, slurried in methanol, treated with methanesulfonic acid (2 equiv), and concentrated. The product was crystallized from ethanol to provide 180 mg the title compound as the bis methanesulfonate salt.

Workup

  1. temperatureheated
  2. temperatureto reflux for 90 minutes
  3. temperaturecooled
  4. customquenched with 1N HCl(0.84 mL)
  5. custompartitioned between water and ethyl acetate
  6. customThe insoluble solid was collected
  7. washwashed with ethyl acetate
  8. concentrationconcentrated
  9. customThe product was crystallized from ethanol

Sources & evidence

ORD record
ord-59444b09c5334e0fb9630ae5b7d8b27c
Source dataset
uspto-grants-2000_12
Patent number
US06166019

Reaction notes

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