Dicyclohexylcarbodiimide → N-Hydroxysulfosuccinimide

HRID 2221295

反応式

HRID 2221295 の反応式
[Na].[OH:2][N:3]1[C:7](=[O:8])[CH2:6][CH:5]([S:9]([OH:12])(=[O:11])=[O:10])[C:4]1=[O:13].C1(N=C=NC2CCCCC2)CCCCC1>CC(N(C)C)=O>[OH:2][N:3]1[C:7](=[O:8])[CH2:6][CH:5]([S:9]([OH:12])(=[O:10])=[O:11])[C:4]1=[O:13]

参加物

4

反応物 2

HCID 10868DicyclohexylcarbodiimideHCID 86222747HCID 86222747、化合物

生成物 1

HCID 133909N-Hydroxysulfosuccinimide

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

L-DM1-TPA (6, 2 mg 0.002 mmol) was dissolved in dimethylacetamide (0.25 mL), to which N-hydroxysulfosuccinimide sodium salt (1.0 mg, 0.0046 mmol) and dicyclohexylcarbodiimide (1.0 mg, 0.0048 mmol) were added. After 3 hours, 0.5 mL of diisopropyl alcohol was added and the resulting precipitate was removed by filtration. HPLC analysis (Vydac C-18 column, 10×250 C18 column, 30° C., flow rate 4.75 mL/min, 50 mM triethylammonium formate pH 3.8 buffer with a linear methanol gradient (30% to 90% over 30 minutes) of the filtrate showed two major peaks, one for unreacted L-DM1-TPA at 22 min and one for L-DM1-TPA sulfosuccinimidyl ester at 19 min. The compound eluting at 19 min was isolated and analyzed by mass spectrometry showing that it had the expected peak consistent with the disodiated molecular ion (M++2Na) of 3a, m/e 1091.4. Further fragmentation of the 1091.4 ion gave predictable daughter ions, m/e 1073.4 (M++2Na—H2O), 874.4 (M++2Na-sodiated N-hydroxysulfosuccinimide).

後処理

  1. additionwere added
  2. customthe resulting precipitate was removed by filtration
  3. customVydac C-18 column, 10×250 C18 column, 30° C., flow rate 4.75 mL/min, 50 mM triethylammonium formate pH 3.8
  4. custombuffer with a linear methanol gradient (30% to 90% over 30 minutes) of the filtrate
  5. customat 22 min
  6. waitone for L-DM1-TPA sulfosuccinimidyl ester at 19 min
  7. washThe compound eluting at 19 min
  8. customwas isolated

出典と根拠

ORDレコード
ord-10f6d1a4d30a45e8aa002c456c556f43
出典データセット
uspto-grants-2008_05
特許番号
US07368565B2

関連ノート

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