N-Hydroxysuccinimide → N-(3-dihydroxyboryl-phenyl)succinamic acid, succinimidyl ester

HRID 1489336

反応式

HRID 1489336 の反応式
[OH:1][B:2]([OH:17])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][CH:8]=1.O[N:19]1[C:23](=[O:24])[CH2:22][CH2:21][C:20]1=[O:25]>CN(C=O)C>[OH:1][B:2]([OH:17])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[CH2:11][CH2:12][C:13]([O:15][N:19]2[C:23](=[O:24])[CH2:22][CH2:21][C:20]2=[O:25])=[O:14])[CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 80170N-HydroxysuccinimideHCID 208171Succinanilic acid, 3'-(dihydroxyboryl)-

生成物 1

HCID 86750205N-(3-dihydroxyboryl-phenyl)succinamic acid, succinimidyl ester収率 59.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-(3-dihydroxyborylphenyl)succinamic acid (16.0 grams, 0.063 mole) is dissolved in dry DMF (80 ml). To the solution is added N,N-dicyclohexylcarbodiimide (14.3 grams, 0.069 mole) followed by N-hydroxysuccinimide (8.05 grams, 0.070 mole). The reaction is stirred overnight at room temperature. N,N-dicyclohexylurea is filtered from the solution, and the filtrate extracted with ethyl acetate (200 ml). The extract is washed with water (3×400 ml) and saturated NaCl (400 ml). The water wash was back-extracted with ethyl acetate (200 ml), the extracts combined, dried over anhydrous Na2SO4, and concentrated on a rotary evaporator to afford 12.5 grams (57% yield) of N-(3-dihydroxyboryl-phenyl)succinamic acid, succinimidyl ester. Purity estimated at 98% by TLC (CHCl3 /CH3OH/CH3COOH; 85:10:5), Rf =0.7. The structure was confirmed by 300 MHz, 1H NMR spectrometry in d6 -DMSO.

後処理

  1. filtrationN,N-dicyclohexylurea is filtered from the solution
  2. extractionthe filtrate extracted with ethyl acetate (200 ml)
  3. washThe extract is washed with water (3×400 ml) and saturated NaCl (400 ml)
  4. washThe water wash
  5. extractionwas back-extracted with ethyl acetate (200 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated on a rotary evaporator

出典と根拠

ORDレコード
ord-d2c0590f4e51485b984c173d80adfe9b
出典データセット
uspto-grants-1997_10
特許番号
US05677431

関連ノート

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