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

HRID 1765686Notes

Reaction equation

HRID 1765686 reaction equation
[OH:1][CH:2]([C:32]1[O:33][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:35][N:36]=1)[CH:3]([NH:8][C:9]([CH:11]([NH:23][C:24]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:25])[CH2:12][S:13]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])=[O:14])=[O:10])[CH2:4][CH2:5][CH2:6][CH3:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:17]1([CH2:16][S:13]([CH2:12][CH:11]([NH:23][C:24]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)=[O:25])[C:9](=[O:10])[NH:8][CH:3]([C:2]([C:32]2[O:33][C:34]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[N:35][N:36]=2)=[O:1])[CH2:4][CH2:5][CH2:6][CH3:7])(=[O:15])=[O:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 22607107sodium thiosulfate NaHCO3HCID 86590020Morpholine-4-carboxylic acid (1-{1-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-methyl]-pentylcarbamoyl}-2-phenylmethane-sulfonyl-ethyl)-amide

Product 1

HCID 11169338Morpholine-4-carboxylic acid {2-phenylmethanesulfonyl-1-[1-(5-phenyl-[1,3,4]oxadiazole-2-carbonyl)-pentylcarbamoyl]-ethyl}-amideYield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Morpholine-4-carboxylic acid (1-{1-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-methyl]-pentylcarbamoyl}-2-phenylmethane-sulfonyl-ethyl)-amide (150 mg, 0.25 mmol), in MeCl2 (5 ml), was treated with Dess-Martin periodinane (183 mg, 0.43 mmol) at room temperature. After stirring for 1 hour, 5 ml of saturated Na2S2O3—NaHCO3 were added. After a further 0.5 hours, the reaction mixture was extracted with ethyl acetate, washed with brine, dried with MgSO4 and concentrated. The residue was purified with silica gel column chromatography to yield morpholine-4-carboxylic acid {2-phenylmethanesulfonyl-1-[1-(5-phenyl-[1,3,4]oxadiazole-2-carbonyl)-pentylcarbamoyl]-ethyl}-amide (84 mg); H1 NMR(DMSO-d): 8.71 (1H, d, J=6.6 Hz, NH), 8.12–8.05 (2H, m), 7.75–7.59 (3H, m), 7.38–7.36 (5H, m), 7.04 (1H, d, J=8.1 Hz, NH), 5.12–5.01 (1H, m), 4.84.65 (1H, m), 4.47 (2H, s), 3.58–3.46 (4H, m), 3.35–3.2 (6H, m), 2.05–1.85 (1H, m), 1.8–1.65 (1H, m), 1.5–1.2 (4H, m), 0.87 (3H, t, J=6.9 Hz, CH3); MS: 596.8 9M−1), 598.6 (M+1).

Workup

  1. waitAfter a further 0.5 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-974db350bdf3426096c931730e89010c
Source dataset
uspto-grants-2007_06
Patent number
US07226921B2

Reaction notes

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