Triacetoxyperiodinane → HCID 86663259, compound

HRID 337164Notes

Reaction equation

HRID 337164 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1([NH:26][C:27](=[O:55])[C:28]2[CH:33]=[C:32]([N:34]3[CH:39]=[CH:38][N:37]=[C:36]([NH:40][C@@H:41]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C@@H:42]([CH3:45])[CH2:43][OH:44])[C:35]3=[O:52])[C:31]([CH3:53])=[C:30]([F:54])[CH:29]=2)[CH2:25][CH2:24]1>C(Cl)Cl>[CH:23]1([NH:26][C:27](=[O:55])[C:28]2[CH:33]=[C:32]([N:34]3[CH:39]=[CH:38][N:37]=[C:36]([NH:40][C@@H:41]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C@@H:42]([CH3:45])[CH:43]=[O:44])[C:35]3=[O:52])[C:31]([CH3:53])=[C:30]([F:54])[CH:29]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66689740HCID 66689740, compound

Product 1

HCID 86663259HCID 86663259, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22 °C

Procedure

A solution of Dess-Martin Periodinane (0.911 g) in DCM (8 mL) was added dropwise to a solution of N-cyclopropyl-3-fluoro-5-[3-{[(1R,2R)-3-hydroxy-2-methyl-1-phenylpropyl]amino}-2-oxopyrazin-1(2H)-yl]-4-methylbenzamide (Example 328d, 0.64 g) in DCM (8 mL) at 22° C. The resulting mixture was stirred at 22° C. for 30 min. The reaction mixture was quenched with sat. aqueous Na2S2O3 and sat. aqeuous NaHCO3 and stirred for a further 15 min and then extracted into DCM. The organic extracts were combined, dried (MgSO4) and concentrated in vacuo to give the subtitle compound as a solid (0.6 g).

Workup

  1. customThe reaction mixture was quenched with sat. aqueous Na2S2O3 and sat. aqeuous NaHCO3
  2. stirringstirred for a further 15 min
  3. extractionextracted into DCM
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69c01eccf1a446d9a69c7a8a076470d2
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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