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Hydroxyamine hydrochloride → N-(3-{[(9-(hydroxyimino)-7-{[(3-hydroxyphenyl)amino]sulfonyl}-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide

HRID 2120917
ノート
印刷プレビュー

反応式

HRID 2120917 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:24]=[C:23]3[C:15]([C:16]4[CH:17]=[CH:18][C:19]([S:26]([NH:29][C:30]5[CH:31]=[C:32]([NH:36][C:37](=[O:39])[CH3:38])[CH:33]=[CH:34][CH:35]=5)(=[O:28])=[O:27])=[CH:20][C:21]=4[C:22]3=O)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:41][OH:42]>N1C=CC=CC=1>[OH:42][N:41]=[C:22]1[C:21]2[CH:20]=[C:19]([S:26]([NH:29][C:30]3[CH:31]=[C:32]([NH:36][C:37](=[O:39])[CH3:38])[CH:33]=[CH:34][CH:35]=3)(=[O:27])=[O:28])[CH:18]=[CH:17][C:16]=2[C:15]2[C:23]1=[CH:24][C:12]([S:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1)(=[O:11])=[O:10])=[CH:13][CH:14]=2
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 443297Hydroxyamine hydrochlorideHCID 9985345N-(3-{[(7-{[(3-Hydroxyphenyl)amino]sulfonyl}-9-oxo-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide

生成物 1

HCID 85117338N-(3-{[(9-(hydroxyimino)-7-{[(3-hydroxyphenyl)amino]sulfonyl}-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide収率 40%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

The product from Example 6A (223 mg, 0.396 mmol) in pyridine (3 mL) was treated with hydroxylamine hydrochloride (30 mg, 0.435 mmol) and heated at reflux. After 30 minutes, the mixture was allowed to cool to ambient temperature and partitioned between ethyl acetate and H2O. The separated organic phase was washed with 1 N HCl, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (75% ethyl acetate/hexanes) to provide the title compound as a light yellow solid (91 mg, 40% yield). 1H NMR (300 MHz, DMSO-d6) δ 13.32 (bs, 1H), 10.2-10.4 (bs, 2H), 9.89 (s, 1H), 9.43 (d, 1H), 8.75 (m, 1H), 8.03-8.17 (m, 3H), 7.8-7.95 (m, 2H), 7.45 (m, 1H), 7.25 (m, 1H), 7.1 (m, 1H), 6.98 (m, 1H), 6.75 (m, 1H), 6.58 (m, 1H), 6.52 (m, 1H), 6.4 (m, 1H), 1.98 (s, 3H); MS (ESI) 577 (M−H)−.

後処理

  1. temperatureheated
  2. temperatureat reflux
  3. custompartitioned between ethyl acetate and H2O
  4. washThe separated organic phase was washed with 1 N HCl, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (75% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-9928e015f54e4c43a8b3419b2a78537f
出典データセット
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06693136B1

反応ノート

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