Triacetoxyperiodinane → HCID 58847437, compound

HRID 1272065Notes

Reaction equation

HRID 1272065 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:29]1[CH:34]=[CH:33][C:32]([O:35][C:36]2[CH:41]=[CH:40][N:39]=[C:38]3[CH:42]=[C:43]([C:45]([N:47]4[CH2:51][CH2:50][C@@H:49]([O:52][CH3:53])[CH2:48]4)=[O:46])[S:44][C:37]=23)=[CH:31][CH:30]=1)[C:25]([NH:27][CH3:28])=[O:26].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:53][O:52][C@@H:49]1[CH2:50][CH2:51][N:47]([C:45]([C:43]2[S:44][C:37]3[C:38](=[N:39][CH:40]=[CH:41][C:36]=3[O:35][C:32]3[CH:33]=[CH:34][C:29]([C:24](=[O:23])[C:25]([NH:27][CH3:28])=[O:26])=[CH:30][CH:31]=3)[CH:42]=2)=[O:46])[CH2:48]1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58847435HCID 58847435, compound

Product 1

HCID 58847437HCID 58847437, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Dess-Martin reagent (48 mg, 0.114 mmol) in 1.5 mL of CH2Cl2 cooled to 0° C., was added dropwise a solution of 2-hydroxy-2-{4-[2-((R)-3-methoxy-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-phenyl}-N-methyl-acetamide (Example 77) (42 mg, 0.095 mmol) in 1.5 mL of CH2Cl2. The mixture was stirred at 0° C. to room temperature for one hour. Saturated aqueous NaHCO3 solution was added, and the mixture was extracted with CH2Cl2 and a small amount of MeOH. The combined organic phase was dried over Na2SO4, concentrated, and purified by flash column chromatography eluting with EtOAc:CH2Cl2:MeOH (1:1:0.04) to provide 30 mg white solid as the compound of Example 78. 1H NMR (300 MHz, CD3OD) δ 8.47 (d, 1H, J=5.47 Hz), 8.17 (d, 2H, J=8.66 Hz), 7.28 (d, 2H, J=8.66 Hz), 7.78–7.62 (m, 1H), 6.81 (d, 1H, J=5.47 Hz), 4.08–3.76 (m, 5H), 3.75–3.52 (m, 3H), 2.78 (s, 3H), 2.30–1.97 (m, 2H). LCMS (ESI+) [M+H]/z Calc'd 440, found 440. Anal. (C22H21N3O5S.0.4CH2Cl2) C, H, N.

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe combined organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by flash column chromatography
  5. washeluting with EtOAc:CH2Cl2:MeOH (1:1:0.04)

Sources & evidence

ORD record
ord-8f139f115b364fe4a8fbf486988a9f41
Source dataset
uspto-grants-2007_04
Patent number
US07208500B2

Reaction notes

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