Methanesulfonic Acid → HCID 72784234, compound

HRID 402223Notes

Reaction equation

HRID 402223 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:25]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:24][CH2:23][CH2:22][C:21]([C:30]([NH:32][C:33]4[CH:38]=[CH:37][C:36]([S:39]([CH2:41][C:42]5[N:46]([CH2:47][CH2:48][CH3:49])[CH:45]=[N:44][CH:43]=5)=[O:40])=[CH:35][CH:34]=4)=[O:31])=[CH:20][C:19]=3[CH:50]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[CH3:51][S:52]([OH:55])(=[O:54])=[O:53]>C(OCC)(=O)C>[CH3:51][S:52]([OH:55])(=[O:54])=[O:53].[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:25]([CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:24][CH2:23][CH2:22][C:21]([C:30]([NH:32][C:33]4[CH:34]=[CH:35][C:36]([S:39]([CH2:41][C:42]5[N:46]([CH2:47][CH2:48][CH3:49])[CH:45]=[N:44][CH:43]=5)=[O:40])=[CH:37][CH:38]=4)=[O:31])=[CH:20][C:19]=3[CH:50]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 6320532HCID 6320532, compound

Product 1

HCID 72784234HCID 72784234, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (−)-8-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[[1-propyl-1H-imidazol-5-yl]methyl]sulfinyl]phenyl]-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxamide (100 mg) in ethyl acetate (4 ml) was added dropwise a solution of methanesulfonic acid (9.31 μl) in ethyl acetate (2 ml) with vigorous stirring, after which the mixture was stirred under light shielding overnight. The precipitated crystals were filtered, and further washed with ethyl acetate (5 ml), followed by drying under reduced pressure. The resulting crystals were recrystallized from 2-butanone (4 ml) to give (−)-8-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[[1-propyl-1H-imidazol-5-yl]methyl]sulfinyl]phenyl]-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxamide methanesulfonate (88.4 mg) as yellow crystals (Compound 14).

Workup

  1. filtrationThe precipitated crystals were filtered
  2. washfurther washed with ethyl acetate (5 ml)
  3. customby drying under reduced pressure
  4. customThe resulting crystals were recrystallized from 2-butanone (4 ml)

Sources & evidence

ORD record
ord-00486394d2974d90951ad71a8a534dc3
Source dataset
uspto-grants-2014_06
Patent number
US08741943B2

Reaction notes

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