Sodium Thiosulfate → HCID 58619487, compound

HRID 1796181Notes

Reaction equation

HRID 1796181 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[CH:32]([OH:59])[CH:33]([NH:36][C:37](=[O:58])[C@@H:38]([CH:48]([F:57])[C:49]([N:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1)=[O:50])[CH2:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:34][CH3:35].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[O:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[C:32]([CH:33]([NH:36][C:37](=[O:58])[C@@H:38]([CH:48]([F:57])[C:49]([N:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1)=[O:50])[CH2:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:34][CH3:35])=[O:59]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86604628HCID 86604628, compound

Product 1

HCID 58619487HCID 58619487, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Dess-Martin Periodinane (15 wt % in DCM, 0.15 mmol, 424 mg) was added to a solution of (S)-2-(1-Fluoro-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid[1-(benzoxazol-2-yl-hydroxy-methyl)-propyl]-amide (0.074 mmol) in dry methylene chloride and stirred for three hours. The reaction was quenched with Na2S2O3 (0.37 mmol, 56 mg) in aqueous NaHCO3, the organic layer was separated, the aqueous extracted once more with methylene chloride, the organic extracts were dried over Na2SO4 and concentrated under reduced pressure. Column chromatography on silica eluting with a mixture of ethyl acetate and methylene chloride gave the title compound as a white solide (30 mg).

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous extracted once more with methylene chloride
  3. dry with materialthe organic extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. additionColumn chromatography on silica eluting with a mixture of ethyl acetate and methylene chloride

Sources & evidence

ORD record
ord-6863727ead5047ae9fc81ee55be807c2
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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