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Methanesulfonic Acid → HCID 178505300, compound

HRID 2111695
Notes
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Reaction equation

HRID 2111695 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent
2×

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-9c907095866e446b9414c8924ff6508d
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07521445B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes