Triacetoxyperiodinane → Morpholine-4-carboxylic acid[(r)-1-(3,4-dioxo-cyclopentylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide

HRID 460415Notes

Reaction equation

HRID 460415 reaction equation
[OH:1][CH:2]1[CH:6]([OH:7])[CH2:5][CH:4]([NH:8][C:9]([C@@H:11]([NH:23][C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:25])[CH2:12][S:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:15])=[O:14])=[O:10])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:7]=[C:6]1[C:2](=[O:1])[CH2:3][CH:4]([NH:8][C:9]([C@@H:11]([NH:23][C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:25])[CH2:12][S:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:14])=[O:15])=[O:10])[CH2:5]1

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 86612926HCID 86612926, compound

Product 1

HCID 10182449Morpholine-4-carboxylic acid[(r)-1-(3,4-dioxo-cyclopentylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of morpholine-4-carboxylic acid [(R)-1-(3,4-dihydroxy-cyclopentylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide (670 mg, 1.47 mmol) in methylene chloride (40 ml) was treated with Dess-Martin periodinane (624 mg, 1.47 mmol) and the reaction stirred at room temperature overnight. More Dess-Martin periodinane (642 mg, 1.51 mmol) was added and the reaction stirred at room temperature for 6 hours and then overnight. 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, then with ethyl acetate to give morpholine-4-carboxylic acid [(R)-1-(3,4-dioxo-cyclopentylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide as an off white solid (45 mg). 1H NMR (CDCl3): 7.50–7.38 (m, 5H), 6.62 (m, 1H), 5.91 (d, J=5 Hz, 1H), 4.81 (m, 1H), 4.58–4.35 (m, 3H), 3.73–3.61 (m, 5H), 3.44–3.32 (m, 4H), 3.22 (m, 1H), 2.72–2.12 (m, 4H). MS: 452 (MH+).

Workup

  1. stirringthe reaction stirred at room temperature for 6 hours
  2. customovernight
  3. washThe reaction mixture was washed with a solution of Na2S2O3 in water (0.26M)
  4. dry with materialwith saturated aqueous bicarbonate solution, then with water, then dried over Na2SO4
  5. customevaporated under reduced pressure
  6. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-2cb706155e1643ffbe1ed26678010d6b
Source dataset
uspto-grants-2007_03
Patent number
US07196099B2

Reaction notes

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