Triacetoxyperiodinane → HCID 10173146, compound

HRID 1376148Notes

Reaction equation

HRID 1376148 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Si]([O:30][CH2:31][CH:32]([OH:58])[CH2:33][N:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37][CH:36]([NH:44][C:45]([C:47]2[NH:48][C:49]3[C:54]([CH:55]=2)=[CH:53][C:52]([Cl:56])=[CH:51][CH:50]=3)=[O:46])[C:35]1=[O:57])(C(C)(C)C)(C)C>C(Cl)Cl>[Cl:56][C:52]1[CH:53]=[C:54]2[C:49](=[CH:50][CH:51]=1)[NH:48][C:47]([C:45]([NH:44][CH:36]1[CH2:37][C:38]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:34]([CH2:33][C:32](=[O:58])[CH2:31][OH:30])[C:35]1=[O:57])=[O:46])=[CH:55]2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58788455HCID 58788455, compound

Product 1

HCID 10173146HCID 10173146, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin Periodinane (120 mg, 0.28 mmol) was added to a stirring solution of N-[1-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-5-chloro-1H-indole-2-carboxamide (Method 6, 74 mg, 0.14 mmol) in DCM and the reaction was stirred for 2 hours. The reaction was quenched by addition of sat. aqueous NaHCO3 (20 mL) and EtOAc (40 mL) and the organic layer was separated and further washed with acidified (pH 0) sodium metabisulfite (10 mL) and the organic layer was dried (MgSO4), filtered and evaporated. Purification by column chromatography (1:19 MeOH:DCM) afforded the title compound (18 mg, 31%) as a white solid.

Workup

  1. customThe reaction was quenched by addition of sat. aqueous NaHCO3 (20 mL) and EtOAc (40 mL)
  2. customthe organic layer was separated
  3. washfurther washed
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by column chromatography (1:19 MeOH:DCM)

Sources & evidence

ORD record
ord-cc9f4187eff34471b97e2e59c22f2283
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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