Methanesulfonic Acid → HCID 178505300, compound

HRID 456517Notes

Reaction equation

HRID 456517 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]([C@@H:11]2[CH2:13][C@H:12]2[CH2:14][OH:15])=[O:10])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:23][S:24](O)(=[O:26])=[O:25]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]([C@@H:11]2[CH2:13][C@H:12]2[CH2:14][O:15][S:24]([CH3:23])(=[O:26])=[O:25])=[O:10])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 178461366HCID 178461366, compound

Product 1

HCID 178505300HCID 178505300, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Add, dropwise, to a stirring suspension at −20° C. of trans-2-hydroxymethyl-cyclopropanecarboxylic acid trans-(4-methylcyclohexyl)-amide (Example 11c) (2.85 g, 13.5 mmol), triethylamine (3.74 mL, 27.0 mmol) and 4-(dimethylamino)pyridine (0.1 g, 0.82 mmol) in dichloromethane (100 ml) a solution of methanesulfonic acid (1.59 mL, 20.3 mmol) in DCM (10 mL). When the reaction is complete, pour the mixture into ice water and extract the mixture with DCM. Combine the extracts, wash with 0.1N KHSO4, brine, dry over MgSO4 and concentrate under vacuum. Treat the residue with a mixture of isopropanol/heptane and collect the precipitate by filtration to obtain 2.91 g (74%) of solid, MS m/z=290 (M+H)+.

Workup

  1. additionAdd
  2. customat −20° C.
  3. extractionextract the mixture with DCM
  4. washwash with 0.1N KHSO4, brine
  5. dry with materialdry over MgSO4
  6. concentrationconcentrate under vacuum
  7. additionTreat the residue
  8. additionwith a mixture of isopropanol/heptane
  9. customcollect the precipitate
  10. filtrationby filtration

Sources & evidence

ORD record
ord-b74f780a2268462f903fd0dbf3998210
Source dataset
uspto-grants-2007_03
Patent number
US07186724B2

Reaction notes

Loading…