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Triacetoxyperiodinane → Morpholine-4-carboxylic acid {2-phenylmethanesulfonyl-1-[1-(5-phenyl-[1,3,4]oxadiazole-2-carbonyl)-pentylcarbamoyl]-ethyl}-amide

HRID 489636
ノート
印刷プレビュー

反応式

HRID 489636 の反応式
[OH:1][CH:2]([C:32]1[O:33][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:35][N:36]=1)[CH:3]([NH:8][C:9]([CH:11]([NH:23][C:24]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:25])[CH2:12][S:13]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])=[O:14])=[O:10])[CH2:4][CH2:5][CH2:6][CH3:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:17]1([CH2:16][S:13]([CH2:12][CH:11]([NH:23][C:24]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)=[O:25])[C:9](=[O:10])[NH:8][CH:3]([C:2]([C:32]2[O:33][C:34]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[N:35][N:36]=2)=[O:1])[CH2:4][CH2:5][CH2:6][CH3:7])(=[O:15])=[O:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 159087TriacetoxyperiodinaneHCID 22607107sodium thiosulfate NaHCO3HCID 86590020Morpholine-4-carboxylic acid (1-{1-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-methyl]-pentylcarbamoyl}-2-phenylmethane-sulfonyl-ethyl)-amide

生成物 1

HCID 11169338Morpholine-4-carboxylic acid {2-phenylmethanesulfonyl-1-[1-(5-phenyl-[1,3,4]oxadiazole-2-carbonyl)-pentylcarbamoyl]-ethyl}-amide収率 56.2%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

実験手順

Morpholine-4-carboxylic acid (1-{1-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-methyl]-pentylcarbamoyl}-2-phenylmethane-sulfonyl-ethyl)-amide (150 mg, 0.25 mmol), in MeCl2 (5 ml), was treated with Dess-Martin periodinane (183 mg, 0.43 mmol) at room temperature. After stirring for 1 hour, 5 ml of saturated Na2S2O3—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 morpholine-4-carboxylic acid {2-phenylmethanesulfonyl-1-[1-(5-phenyl-[1,3,4]oxadiazole-2-carbonyl)-pentylcarbamoyl]-ethyl}-amide (84 mg); H1 NMR(DMSO-d): 8.71 (1H, d, J=6.6 Hz, NH), 8.12-8.05 (2H, m), 7.75-7.59 (3H, m), 7.38-7.36 (5H, m), 7.04 (1H, d, J=8.1 Hz, NH), 5.12-5.01 (1H, m), 4.8-4.65 (1H, m), 4.47 (2H, s), 3.58-3.46 (4H, m), 3.35-3.2 (6H, m), 2.05-1.85 (1H, m), 1.8-1.65 (1H, m), 1.5-1.2 (4H, m), 0.87 (3H, t, J=6.9 Hz, CH3); MS: 596.8 9M−1), 598.6 (M+1).

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-7ebe3c3861674955a5422ee018955ede
出典データセット
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06977256B2

反応ノート

読み込み中…

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