Triacetoxyperiodinane → Morpholine4-carboxylic acid[(r)-1-(6-oxo-cyclohex-1-enylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide

HRID 460411Notes

Reaction equation

HRID 460411 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4](O)[CH:3]1[NH:9][C:10]([C@@H:12]([NH:24][C:25]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26])[CH2:13][S:14]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:16])=[O:15])=[O:11].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[C:3]([NH:9][C:10]([C@@H:12]([NH:24][C:25]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)=[O:26])[CH2:13][S:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:15])=[O:16])=[O:11])=[CH:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86612924Morpholine-4-carboxylic acid[(r)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide

Product 1

HCID 10114756Morpholine4-carboxylic acid[(r)-1-(6-oxo-cyclohex-1-enylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amideYield 9.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of morpholine-4-carboxylic acid [(R)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide (90 mg, 0.19 mmol) in methylene chloride (6 ml) was treated with Dess-Martin periodinane (162 mg, 0.38 mmol). After stirring at room temperature for 2 hours the reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), then with saturated aqueous bicarbonate solution then with water, then dried over Na2SO4 and then evaporated under reduced pressure. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane to give morpholine4-carboxylic acid [(R)-1-(6-oxo-cyclohex-1-enylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide (8 mg). 1H NMR (CDCl3): 9.00 (s, 1H), 7.82 (t, J=5 Hz, 1H), 7.53–7.38 (m, 5H), 6.06 (d, J=6 Hz, 1H), 5.00 (m, 1H), 4.47–4.27 (m, 2H), 3.85 (m, 1H), 3.77–3.62 (m, 4H), 3.48–3.36 (m, 4H), 3.27 (m, 1H), 2.58–2.46 (m, 4H), 2.08–1.97 (m, 2H). MS: 450 (MH+).

Workup

  1. washwas washed with a solution of Na2S2O3 in water (0.26M)
  2. dry with materialwith saturated aqueous bicarbonate solution then with water, then dried over Na2SO4
  3. customevaporated under reduced pressure
  4. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-455d14757fc4463f9ccb442c8626b351
Source dataset
uspto-grants-2007_03
Patent number
US07196099B2

Reaction notes

Loading…