Triacetoxyperiodinane → Sar-114137

HRID 1796160Notes

Reaction equation

HRID 1796160 reaction equation
[OH:1][CH:2]([C:27]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:29][N:28]=1)[C@@H:3]([NH:6][C:7](=[O:26])[CH:8]([CH2:18][S:19]([CH2:22][CH:23]([CH3:25])[CH3:24])(=[O:21])=[O:20])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11])[CH2:4][CH3:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:25][CH:23]([CH3:24])[CH2:22][S:19]([CH2:18][CH:8]([CH2:9][C:10]([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)=[O:11])[C:7]([NH:6][C@H:3]([C:2]([C:27]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:29][N:28]=1)=[O:1])[CH2:4][CH3:5])=[O:26])(=[O:20])=[O:21]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11635192N-{(S)-1-[Hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-2-(2-methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide

Product 1

HCID 9828551Sar-114137

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-{(S)-1-[Hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-2-(2-methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide (41 mg, 0.076 mmol) in methylene chloride (6 mL) was treated with Dess-Martin periodinane (39 mg, 0.092 mmol) and stirred at room temperature for 90 minutes. The reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), saturated aqueous bicarbonate solution and water, dried over Na2SO4 and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography eluting with a mixture of ethyl acetate and heptane to give 2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-N-[(S)-1-(5-phenyl-1,2,4-oxadiazole-3-carbonyl)-propyl]-butyramide as an off white solid (18 mg) (mixture of diastereoisomers).

Workup

  1. washThe reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), saturated aqueous bicarbonate solution and water
  2. dry with materialdried over Na2SO4
  3. customthe solvent evaporated under reduced pressure
  4. customThe residue was purified by flash chromatography
  5. washeluting with a mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-8f2cf64a27df4753ae152ad9be28f2cc
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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