Dicyclohexylcarbodiimide → N-Hydroxysulfosuccinimide

HRID 2221295

반응식

HRID 2221295 반응식
[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]

참가 물질

4

반응물 2

HCID 10868DicyclohexylcarbodiimideHCID 86222747HCID 86222747, 화합물

생성물 1

HCID 133909N-Hydroxysulfosuccinimide

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-10f6d1a4d30a45e8aa002c456c556f43
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368565B2

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