Sodium Thiosulfate → HCID 59857994, compound

HRID 1671618Notes

Reaction equation

HRID 1671618 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([N:30]1[CH2:34][CH:33]([OH:35])[CH:32]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[N:38]=2)[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[C:23]([O:27][C:28]([N:30]1[CH2:34][C:33](=[O:35])[CH:32]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[N:38]=2)[CH2:31]1)=[O:29])([CH3:25])([CH3:26])[CH3:24]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 59858003HCID 59858003, compound

Product 1

HCID 59857994HCID 59857994, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of Dess-Martin periodinane (0.0014 mol) in 10 mL CH2Cl2 was added a solution of 3-(6-tert-butoxycarbonylamino-pyridin-2-ylmethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester III-2 (0.001 mol) in 5 mL CH2Cl2 and the reaction mixture was stirred at room temperature for 18 h. 1 M Na2S2O3 (10 mL) was added to the reaction, and after stirring for 10 min, the reaction mixture was extracted with CH2Cl2 (10 mL×3). The combined organic layers were washed with 5% aqueous NaHCO3 (20 mL×3) and brine (20 mL×2). The organic layer was dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, hexanes:EtOAc, 8:2) to give pure product (96%).

Workup

  1. stirringafter stirring for 10 min
  2. extractionthe reaction mixture was extracted with CH2Cl2 (10 mL×3)
  3. washThe combined organic layers were washed with 5% aqueous NaHCO3 (20 mL×3) and brine (20 mL×2)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, hexanes:EtOAc, 8:2)

Sources & evidence

ORD record
ord-35c1a329c41946649ea7593443ff231e
Source dataset
uspto-grants-2011_08
Patent number
US07994326B2

Reaction notes

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