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

HRID 1830195ノート

反応式

HRID 1830195 の反応式
[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

参加物

4

反応物 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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-60a92c94734740359d4c48d1a79e2d11
出典データセット
uspto-grants-2006_06
特許番号
US07064123B1

反応ノート

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