Water → HCID 86622009, compound

HRID 1099138Notes

Reaction equation

HRID 1099138 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][C@@H:25]([N:27]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[C:46]2[N:50]([C:51]([C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[N:49]=[N:48][N:47]=2)=[CH:36][CH:35]=1)[C:28](=[O:32])[CH2:29][CH2:30][CH3:31])[CH3:26].O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH3:26][C@H:25]([N:27]([CH2:33][C:34]1[CH:35]=[CH:36][C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[C:46]2[N:50]([C:51]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)[N:49]=[N:48][N:47]=2)=[CH:38][CH:39]=1)[C:28](=[O:32])[CH2:29][CH2:30][CH3:31])[CH:24]=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 66813907HCID 66813907, compound

Product 1

HCID 86622009HCID 86622009, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (971 mg, 2.3 mmol) was added to a solution of intermediate (5b) (474 mg, 0.8 mmol) in DCM (20 mL) at room temperature. After 30 minutes, water (20 mL) and saturated aqueous sodium thiosulfate (20 mL) was added. The mixture was extracted with DCM (3×30 mL), washed with saturated aqueous NaCl (20 mL), dried over MgSO4, and concentrated in vacuo. Silica gel chromatography gave intermediate (5c) as a white solid (411 mg).

Workup

  1. extractionThe mixture was extracted with DCM (3×30 mL)
  2. washwashed with saturated aqueous NaCl (20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2ef4d5a78af461f82c92a7b5191a93b
Source dataset
uspto-grants-2012_03
Patent number
US08143298B2

Reaction notes

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