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

HRID 460411ノート

反応式

HRID 460411 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-455d14757fc4463f9ccb442c8626b351
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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