Methanesulfonyl chloride → HCID 67057891, compound

HRID 2361702Notes

Reaction equation

HRID 2361702 reaction equation
C([C:3]1([C:21]([O-:23])=[O:22])[CH:9](O)[CH2:8][CH2:7][N:6]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:5][CH2:4]1)C.CS(Cl)(=O)=O.[CH2:29]1CCN2C(=NCCC2)C[CH2:30]1>C1COCC1>[N:6]1([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:7][CH2:8][CH:9]=[C:3]([C:21]([O:23][CH2:29][CH3:30])=[O:22])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86652974HCID 86652974, compound

Product 1

HCID 67057891HCID 67057891, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution 1-benzyl 4-ethyl-5-hydroxyazepane-1,4-dicarboxylate (4.4 g, 13.7 mmol) in THF (100 ml) was added MsCl (2.58 ml, 33.6 mmol) and TEA (5.69 ml, 40.5 mmol) in three portions over 16 hours. The mixture was then concentrated, diluted with dichloromethane (100 ml), washed with saturated aqueous NaHCO3 (2×50 ml), dried (MgSO4), filtered and reconcentrated. The residue was dissolved in THF (100 ml) and DBU (3.1 ml, 20.6 mmol) was added and the resulting mixture was heated at 80° C. for 1 hour. The reaction was then concentrated, diluted with dichloromethane (100 ml), washed with saturated aqueous NaHCO3 (3×30 ml), dried (MgSO4), filtered and reconcentrated. The residue was purified via silica FCC (using a gradient of eluents; 9:1 to 7:3 Hexane/EtOAc) to give the title product as colourless oil (2.1 g, 51%).

Workup

  1. concentrationThe mixture was then concentrated
  2. additiondiluted with dichloromethane (100 ml)
  3. washwashed with saturated aqueous NaHCO3 (2×50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. dissolutionThe residue was dissolved in THF (100 ml)
  7. concentrationThe reaction was then concentrated
  8. additiondiluted with dichloromethane (100 ml)
  9. washwashed with saturated aqueous NaHCO3 (3×30 ml)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customThe residue was purified via silica FCC (

Sources & evidence

ORD record
ord-4bb41d28c2684b43ac94ad45a6e2482d
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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