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Phosphate → (5R, 6E)-6-[(10-benzyl-11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepin-8-yl)methylene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

HRID 1744939
ノート
印刷プレビュー

反応式

HRID 1744939 の反応式
P([O-])([O-])([O-])=O.[N+](C1C=CC(C[O:14][C:15]([C:17]2[N:18]3[CH:21]([S:22][CH:23]=2)[C:20]([CH:25](OC(=O)C)[C:26]2[CH:48]=[CH:47][C:29]4[O:30][C:31]5[CH:46]=[CH:45][CH:44]=[CH:43][C:32]=5[C:33](=[O:42])[N:34]([CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:28]=4[CH:27]=2)(Br)[C:19]3=[O:53])=[O:16])=CC=1)([O-])=O>C1COCC1.[Pd]>[CH2:35]([N:34]1[C:33](=[O:42])[C:32]2[CH:43]=[CH:44][CH:45]=[CH:46][C:31]=2[O:30][C:29]2[CH:47]=[CH:48][C:26](/[CH:25]=[C:20]3/[C@@H:21]4[N:18]([C:19]/3=[O:53])[C:17]([C:15]([OH:16])=[O:14])=[CH:23][S:22]4)=[CH:27][C:28]1=2)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=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 2

HCID 1061PhosphateHCID 684449316-[Acetoxy-(10-benzyl-11-oxo-10,11-dihydro-dibenzo[b,f][1,4]oxazepin-8-yl)-methyl]-6-bromo-7oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

生成物 1

HCID 10457946(5R, 6E)-6-[(10-benzyl-11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepin-8-yl)methylene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid収率 24%

試薬・触媒・溶媒 2

HCID 23938
Palladium
触媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A 0.5M phosphate buffer solution (pH 6.5) was added to a solution of 6-[acetoxy-(10-benzyl-11-oxo-10,11-dihydro-dibenzo[b,f][1,4]oxazepin-8-yl)-methyl]-6-bromo-7oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (0.210 g, 0.273 mmole) in THF, followed by 10% Pd—C (0.0546 g). The reaction mixture then was hydrogenated at 40 psi for three hours. Filtered through a celite pad and removed the THF by rotary evaporation, extracted the mixture with ethyl acetate and washed with water and brine. Dried the organic layer with sodium sulfate and filtered and concentrated. Dissolved the NaHCO3 with minimal amount of distal water and added it to the reaction mixture along with a small amount of ethyl acetate until the pH value reaches 7–8, evaporated the ethyl acetate. Purified with reverse phase column (MCI Gel CHP20P) with varying amounts of acetonitrile (0%-20%) in water. Removed the acetonitrile and water by rotary evaporation, and freeze-dried the compound. Obtained the desired material (yellow solid) in 24% yield.Mp: 179° C. 1H NMR (DMSO) δ 1.755–1.825 (s, 1H), 2.497–2.506 (d, 2H), 5.243–5.434 (m, 2H), 6.516–6.770 (m, 1H), 7.039–7.792 (m, 11H).

後処理

  1. filtrationFiltered through a celite pad
  2. customremoved the THF
  3. customby rotary evaporation
  4. extractionextracted the mixture with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialDried the organic layer with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionDissolved the NaHCO3 with minimal amount of distal water
  10. additionadded it to the reaction mixture along with a small amount of ethyl acetate until the pH value
  11. customevaporated the ethyl acetate
  12. customPurified with reverse phase column (MCI Gel CHP20P) with varying amounts of acetonitrile (0%-20%) in water
  13. customRemoved the acetonitrile and water
  14. customby rotary evaporation
  15. customfreeze-dried the compound

出典と根拠

ORDレコード
ord-9c0b7bbb1d4d42d5970fee150cc265cc
出典データセット
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07018997B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート