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

HRID 460415ノート

反応式

HRID 460415 の反応式
[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

参加物

4

反応物 2

HCID 159087Triacetoxyperiodinane2 回HCID 86612926HCID 86612926、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-2cb706155e1643ffbe1ed26678010d6b
出典データセット
uspto-grants-2007_03
特許番号
US07196099B2

反応ノート

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