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

HRID 460415노트

반응식

HRID 460415 반응식
[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

참가 물질

4

반응물 2

HCID 159087Triacetoxyperiodinane2회HCID 86612926HCID 86612926, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-2cb706155e1643ffbe1ed26678010d6b
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196099B2

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