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Phosphate → (5R,6Z)-6-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylmethylene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 2216627
ノート
印刷プレビュー

反応式

HRID 2216627 の反応式
C(O[CH:5]([C:28]1[CH:36]=[C:31]2[CH2:32][O:33][CH2:34][CH2:35][N:30]2[N:29]=1)[C:6]1(Br)[C:12](=[O:13])[N:11]2[C@@H:7]1[S:8][CH:9]=[C:10]2[C:14]([O:16]CC1C=CC([N+]([O-])=O)=CC=1)=[O:15])(=O)C.P([O-])([O-])([O-])=O>C1COCC1.[Pd]>[N:29]1[N:30]2[C:31]([CH2:32][O:33][CH2:34][CH2:35]2)=[CH:36][C:28]=1/[CH:5]=[C:6]1\[C@@H:7]2[N:11]([C:12]\1=[O:13])[C:10]([C:14]([OH:16])=[O:15])=[CH:9][S:8]2
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 118472844-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

生成物 1

HCID 11847461(5R,6Z)-6-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylmethylene)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of 4-nitrobenzyl (5R)-6-[(acetyloxy)(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.35 g, 0.6 mmol) in THF (20 ml), under nitrogen, was added 20 ml of a phosphate buffer solution (0.5M, pH 6.5), and 120 mg of 10% Pd/C. The mixture was hydrogenated at 40–50 psi for 3 hr, and then filtered through Celite. The filter pad was washed with THF, and the filtrate was extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate and evaporated. The residue was washed with ether to give; 0.09 g of a yellow solid; HRMS: calcd for C13H11N3O4S, 305.0470; found (ESI+), 306.05434; 1H NMR (DMSO-d6) δ 4.07–4.09 (t, 2H), 4.13–4.17 (t, 2H), 4.82 (s, 2H), 6.36 (s, 1H), 6.55 (s, 1H), 7.17 (s, 1H), 7.55 (s, 1H), 12.80 (bs, 1H).

後処理

  1. filtrationfiltered through Celite
  2. washThe filter pad was washed with THF
  3. extractionthe filtrate was extracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customevaporated
  7. washThe residue was washed with ether
  8. customto give

出典と根拠

ORDレコード
ord-d24c3731c0244bd8834caeb4b4188e69
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07112582B2

反応ノート

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