Triacetoxyperiodinane → HCID 86659091, compound

HRID 1944929Notes

Reaction equation

HRID 1944929 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([C:35]1[CH:36]=[C:37]([S:41]([C:44]2[CH:45]=[C:46]3[C:51](=[C:52]([CH3:54])[CH:53]=2)[N:50]=[CH:49][C:48]([C:55]([NH2:57])=[O:56])=[C:47]3[NH:58][C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([O:65][CH3:66])[CH:60]=2)(=[O:43])=[O:42])[CH:38]=[CH:39][CH:40]=1)=[O:34].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:66][O:65][C:61]1[CH:60]=[C:59]([NH:58][C:47]2[C:46]3[C:51](=[C:52]([CH3:54])[CH:53]=[C:44]([S:41]([C:37]4[CH:38]=[CH:39][CH:40]=[C:35]([C:33](=[O:34])[NH:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=[O:23])[CH:36]=4)(=[O:43])=[O:42])[CH:45]=3)[N:50]=[CH:49][C:48]=2[C:55]([NH2:57])=[O:56])[CH:64]=[CH:63][CH:62]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 669880286-[[3-[(8-Hydroxyoctyl)carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Product 1

HCID 86659091HCID 86659091, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dess-Martin reagent (105 mg, 0.249 mmol) was added to a stirring solution of Intermediate 70 (77 mg, 0.124 mmol) in DMF (2 mL) at rt. The resulting solution was stirred for 3 h and poured into satd. NaHCO3 (50 mL). The precipitate was filtered, washed with H2O, and dried to give the title compound (70 mg) as a yellow solid. The compound was used with no further purification. ES/MS calcd. for C33H37N4O6S+ 617.2. Found m/z=617.3 (M+H)+.

Workup

  1. additionpoured into satd
  2. filtrationThe precipitate was filtered
  3. washwashed with H2O
  4. customdried

Sources & evidence

ORD record
ord-7c48c58290b741a7b01bf1bcd92fb7d7
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

Loading…