Oxalic Acid → HCID 86595572, compound

HRID 1928890Notes

Reaction equation

HRID 1928890 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].[C:51]([OH:56])(=[O:55])[C:52]([OH:54])=[O:53]>C(OCC)(=O)C.C(O)C>[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].[C:51]([O-:56])(=[O:55])[C:52]([O-:54])=[O:53]

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 6320532HCID 6320532, compound

Product 1

HCID 86595572HCID 86595572, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

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 a solution of oxalic acid (6.46 mg) in ethanol (2 ml), after which the solvent was distilled off under reduced pressure. Ethyl acetate (5 ml) was added, and the solvent was again distilled off under reduced pressure, after which ethyl acetate (4 ml) was added, and the mixture was allowed to stand overnight under light shielding. The precipitated crystals were filtered, and further washed with ethyl acetate (5 ml), after which the resultant was dried under reduced pressure 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/oxalate (50 mg) as yellow crystals (Compound 13).

Workup

  1. distillationafter which the solvent was distilled off under reduced pressure
  2. additionEthyl acetate (5 ml) was added
  3. distillationthe solvent was again distilled off under reduced pressure
  4. additionafter which ethyl acetate (4 ml) was added
  5. filtrationThe precipitated crystals were filtered
  6. washfurther washed with ethyl acetate (5 ml)
  7. customafter which the resultant was dried under reduced pressure

Sources & evidence

ORD record
ord-1ab643ad65434812be484e6ac55ca1cc
Source dataset
uspto-grants-2012_05
Patent number
US08183273B2

Reaction notes

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