Triacetoxyperiodinane → 2-Cyclohexylmethyl-n-[1-(5-ethyl-[1,3,4]oxadiazole-2-carbonyl)-butyl]-4-morpholin-4-yl-4-oxo-butyramide

HRID 1830195노트

반응식

HRID 1830195 반응식
[CH:1]1([CH2:7][CH:8]([CH2:25][C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[C:9]([NH:11][CH:12]([CH:16]([C:18]2[O:19][C:20]([CH2:23][CH3:24])=[N:21][N:22]=2)[OH:17])[CH2:13][CH2:14][CH3:15])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>>[CH:1]1([CH2:7][CH:8]([CH2:25][C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[C:9]([NH:11][CH:12]([C:16]([C:18]2[O:19][C:20]([CH2:23][CH3:24])=[N:21][N:22]=2)=[O:17])[CH2:13][CH2:14][CH3:15])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 3

HCID 159087TriacetoxyperiodinaneHCID 18470521Sodium bicarbonate sodium sulfiteHCID 220540862-cyclohexylmethyl-N-{1-[(5-ethyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-butyl}-4-morpholin-4-yl-4-oxo-butyramide

생성물 1

HCID 220539852-Cyclohexylmethyl-n-[1-(5-ethyl-[1,3,4]oxadiazole-2-carbonyl)-butyl]-4-morpholin-4-yl-4-oxo-butyramide

실험 절차

This amide was treated with Dess-Martin periodinane (239 mg, 0.48 mmol) at room temperature. After stiffing for 1 hour, 5 mls of saturated Na2SO3—NaHCO3 were added. After a further 0.5 hours, the reaction mixture was extracted with ethyl acetate, washed with brine, dried with MgSO4 and concentrated. The residue was purified with silica gel column chromatography to yield 65 mg of 2-cyclohexylmethyl-N-[1-(5-ethyl-[1,3,4]oxadiazole-2-carbonyl)-butyl]-4-morpholin-4-yl-4-oxo-butyramide; H1 NMR (DMSO-d): 8.6, 8.51(11H, dd, J=6.8 Hz, J=5.6 Hz, NH, diastereomeric), 4.98(−4.88 (1H, m), 3.6–3.25(8H, m), 3–2.9(2H, q, J=7.6 Hz), 2.9–2.75(1H, m), 2.5–2.4(1H, m), 2.3–2.1(1H, m), 1.9–1.7(2H, m), 1.7–1.4(7H, m), 1.4–1.2(2H, m), 1.28(3H, t), 1.2–1(6H, m), 0.88(3H, t); MS: 461.4(M−1), 463.4(M+1), 485.4(M+Na).

후처리

  1. waitAfter a further 0.5 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography

출처 및 근거

ORD 기록
ord-60a92c94734740359d4c48d1a79e2d11
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07064123B1

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