Methanesulfonyl chloride → HCID 86635929, compound

HRID 561861Notes

Reaction equation

HRID 561861 reaction equation
[CH:1]1([N:4]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=2[Cl:39])[C:5](=[O:30])[CH:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]3[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[Cl:29])=[CH:13][CH:12]=2)[CH2:7][CH2:8]O)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CS(Cl)(=O)=O.[N-:54]=[N+:55]=[N-:56].[Na+]>C(Cl)Cl.O>[N:54]([CH2:8][CH2:7][CH:6]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[Cl:29])=[CH:15][CH:16]=1)[C:5]([N:4]([CH:1]1[CH2:2][CH2:3]1)[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=1[Cl:39])=[O:30])=[N+:55]=[N-:56]

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 81531DiisopropylethylamineHCID 66762160HCID 66762160, compound

Product 1

HCID 86635929HCID 86635929, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Cyclopropyl-N-(2,3-dichlorobenzyl)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-4-hydroxybutanamide from the previous step (1 eq.) and Hunig's base (3.5 eq.) were combined in CH2Cl2 (0.024 M). At −78° C., methanesulfonyl chloride (1.5 eq) was added and the reaction mixture was stirred at −78° C. for 10 min and at 0° C. for 10 min. The resulting mixture was quenched with sat. aq. NaHCO3 and extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered and the filtrate concentrated in vacuo. The resulting residue was taken up in DMF (0.06 M) and added sodium azide (5 eq). This mixture was then allowed to stir at RT for 24 h. The resulting mixture was poured into water and extracted with ether. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of column chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a viscous oil.

Workup

  1. customThe resulting mixture was quenched with sat. aq. NaHCO3
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. stirringto stir at RT for 24 h
  7. extractionextracted with ether
  8. washThe combined organic extracts were washed with water and brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated in vacuo
  12. customPurification of the crude product
  13. customthus obtained by way of column chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-43941b7c215347f18a13047672979965
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

Loading…