Sodium Thiosulfate → morpholine-4-carboxylic acid ((S)-3,3-difluoro-1-{(S)-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazole-2-carbonyl]-propylcarbamoyl}-hexyl)-amide

HRID 1455599Notes

Reaction equation

HRID 1455599 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]([F:63])([CH2:60][CH2:61][CH3:62])[CH2:25][C@H:26]([NH:51][C:52]([N:54]1[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1)=[O:53])[C:27](=[O:50])[NH:28][C@H:29]([CH:32]([OH:49])[C:33]1[O:34][C:35]([C:38]2[CH:43]=[CH:42][C:41]([O:44][C:45]([F:48])([F:47])[F:46])=[CH:40][CH:39]=2)=[N:36][N:37]=1)[CH2:30][CH3:31].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:63][C:24]([F:23])([CH2:60][CH2:61][CH3:62])[CH2:25][C@H:26]([NH:51][C:52]([N:54]1[CH2:55][CH2:56][O:57][CH2:58][CH2:59]1)=[O:53])[C:27](=[O:50])[NH:28][C@H:29]([C:32]([C:33]1[O:34][C:35]([C:38]2[CH:43]=[CH:42][C:41]([O:44][C:45]([F:46])([F:47])[F:48])=[CH:40][CH:39]=2)=[N:36][N:37]=1)=[O:49])[CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86607348morpholine-4-carboxylic acid [(S)-3,3-difluoro-1-((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl)-propylcarbamoyl)-hexyl]-amide

Product 1

HCID 11410760morpholine-4-carboxylic acid ((S)-3,3-difluoro-1-{(S)-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazole-2-carbonyl]-propylcarbamoyl}-hexyl)-amideYield 65.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Dess-Martin Periodinane (15 wt % in DCM, 0.58 gm, 0.21 mmol) is added to a solution of morpholine-4-carboxylic acid [(S)-3,3-difluoro-1-((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl}-propylcarbamoyl)-hexyl]-amide (61 mg, 0.10 mmol) in dry methylene chloride (8 mL) and stirred at room temperature for 3 hrs. The reaction is quenched with a solution of Na2S2O3 (81.43 mg, 0.50 mmol) in aqueous NaHCO3. The organic layer is separated and the aqueous extracted with dichloromethane. The organic extracts are dried over sodium sulfate and concentrated under reduced pressure. Column chromatography on silica eluting with a mixture of methylene chloride and ethyl acetate gives morpholine-4-carboxylic acid ((S)-3,3-difluoro-1-{(S)-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazole-2-carbonyl]-propylcarbamoyl}-hexyl)-amide as a powder (39 mg).

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous extracted with dichloromethane
  3. dry with materialThe organic extracts are dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionColumn chromatography on silica eluting with a mixture of methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-883f872887644de792e3157cd7a69aef
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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