Triacetoxyperiodinane → Morpholine carboxylic acid {2-cyclopropylmethanesulfonyl-1-[1-(5-phenyl-1,2,4-oxadiazole-3-carbonyl)-propylcarbamoyl]-ethyl}-amide

HRID 489640Notes

Reaction equation

HRID 489640 reaction equation
[CH:1]1([CH2:4][S:5]([CH2:8][CH:9]([NH:29][C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:31])[C:10](=[O:28])[NH:11][CH:12]([CH:15]([OH:27])[C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][N:17]=2)[CH2:13][CH3:14])(=[O:7])=[O:6])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:1]1([CH2:4][S:5]([CH2:8][CH:9]([NH:29][C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:31])[C:10](=[O:28])[NH:11][CH:12]([C:15]([C:16]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:18][N:17]=2)=[O:27])[CH2:13][CH3:14])(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86590022Morpholine-4-carboxylic acid (2-cyclopropylmethanesulfonyl-1-{1-[hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propylcarbamoyl}-ethyl)-amide

Product 1

HCID 10311723Morpholine carboxylic acid {2-cyclopropylmethanesulfonyl-1-[1-(5-phenyl-1,2,4-oxadiazole-3-carbonyl)-propylcarbamoyl]-ethyl}-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of morpholine-4-carboxylic acid (2-cyclopropylmethanesulfonyl-1-{1-[hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propylcarbamoyl}-ethyl)-amide (183 mg, 0.34 mmol) in methylene chloride (10 mL), Dess-Martin Periodinane (200 mg, 0.47 mmol) was added and stirred at room temperature for 2 hours. The reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), saturated bicarbonate, and water, dried over Na2SO4 and concentrated under reduced pressure. The residue was subjected to flash chromatography eluting with a mixture of ethyl acetate and heptane to give morpholine-4-carboxylic acid {2-cyclopropylmethanesulfonyl-1-[1-(5-phenyl-1,2,4-oxadiazole-3-carbonyl)-propylcarbamoyl]-ethyl}-amide, a mixture of diastereomers, (45 mg) as an off white solid. 1H NMR (CDCl3): 8.22 (d, J=7 Hz, 2H), 7.83, 7.75 (2×d, J=7 Hz, 1H), 7.65 (m, 1H), 7.60-7.51 (m, 2H), 6.10-6.07 (2×d, J=7 Hz, 1H), 5.36 (m, 1H), 5.00-4.86 (m, 1H), 3.79 (m, 1H), 3.74-3.66 (m, 4H), 3.48 (m, 1H), 3.47-3.37 (m, 4H), 3.20-3.07 (m, 2H), 2.24-2.06 (m, 1H), 2.00-1.82 (m, 1H), 1.22 (m, 1H), 1.01 (t, J=7 Hz, 3H), 0.80-0.68 (m, 2H), 0.56-0.38 (m, 2H). MS: 534 (MH+).

Workup

  1. washThe reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), saturated bicarbonate, and water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. washeluting with a mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-139e0ef9faef448d9d77e997153126ea
Source dataset
uspto-grants-2005_12
Patent number
US06977256B2

Reaction notes

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