Sodium Thiosulfate → HCID 178456080, compound

HRID 2212244Notes

Reaction equation

HRID 2212244 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH:11]([OH:16])[C@@H:12]([NH-:15])[CH2:13][CH3:14].[NH:17]=[C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[NH:19]1.C(N(CC)[CH:32]([CH3:34])[CH3:33])(C)C.CC(OI1(OC(C)=O)(OC(C)=O)O[C:48](=[O:49])[C:47]2C=CC=C[C:42]1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]([C@@H:12]([NH:15][C:48](=[O:49])[C@@H:47]([NH:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[N:19]=1)[CH2:42][CH:32]([CH3:33])[CH3:34])[CH2:13][CH3:14])=[O:16]

Participants

9

Reactant 5

HCID 24477Sodium ThiosulfateHCID 81531DiisopropylethylamineHCID 159087TriacetoxyperiodinaneHCID 131725920HCID 131725920, compoundHCID 1357423743-Imino-2,3-dihydroisoindol-1-one

Product 1

HCID 178456080HCID 178456080, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

(S)-[1-(Benzoxazol-2-yl-hydroxy-methyl)-propyl]-amide hydrochloride (90 mg, 0.254 mmol), 3-iminoisoindolinone (100 mg, 0.684 mmol), and N,N-diisopropylethyl-amine (0.2 mL) were dissolved in THF (10 mL) and heated at reflux for 5 h. After dilution with ethyl acetate (150 mL), the solution was washed with saturated aqueous NaHCO3 solution and brine, dried with MgSO4 and evaporated under vacuum. The crude product was dissolved in dry dichloromethane (10 mL) and Dess-Martin Periodinane (400 mg, 0.96 mmol) was added. After stirring at ambient temperature for 1 h, the reaction mixture was diluted with ethyl acetate (150 mL) and treated with 0.26 M Na2S2O3 solution in saturated aqueous NaHCO3. The organic phase was washed with saturated aqueous NaHCO3 and brine, dried with MgSO4 and evaporated. The product was purified by flash chromatography on silica gel (hexane/ethyl acetate 2:1) to yield the title compound (20 mg; 0.045 mmol) as a 1:1 mixture of isomers.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 h
  3. washAfter dilution with ethyl acetate (150 mL), the solution was washed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried with MgSO4
  5. customevaporated under vacuum
  6. dissolutionThe crude product was dissolved in dry dichloromethane (10 mL)
  7. washThe organic phase was washed with saturated aqueous NaHCO3 and brine
  8. dry with materialdried with MgSO4
  9. customevaporated
  10. customThe product was purified by flash chromatography on silica gel (hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-9d22f945774347609de2ae2930966c10
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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