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Chemical Structure| 74648-14-9 Chemical Structure| 74648-14-9

Structure of Di(N-succinimidyl) Pimelate
CAS No.: 74648-14-9

Chemical Structure| 74648-14-9

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Product Details of [ 74648-14-9 ]

CAS No. :74648-14-9
Formula : C15H18N2O8
M.W : 354.31
SMILES Code : O=C(CCCCCC(=O)ON1C(=O)CCC1=O)ON1C(=O)CCC1=O
MDL No. :MFCD01318519
InChI Key :LOJVONPJBWABIQ-UHFFFAOYSA-N
Pubchem ID :13650501

Safety of [ 74648-14-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 74648-14-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 74648-14-9 ]

[ 74648-14-9 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 6066-82-6 ]
  • [ 111-16-0 ]
  • [ 74648-14-9 ]
YieldReaction ConditionsOperation in experiment
71% With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 18.0h; [00350] Heptanedioic acid (1.6 g, 9.99 mmol) was dissolved in tetrahydrofuran (THF) (100 mL), and l-hydroxypyrrolidine-2,5-dione (2.299 g, 19.98 mmol) was then added, followed by the addition of DCC (4.12 g, 19.98 mmol). The mixture was stirred at room temperature for 18 hours until HPLC analysis indicated the completion of the reaction. The solid was removed by filtration through a celite pad, and washed with THF (3 x 2 mL). The combined filtrate was concentrated and purified by flash chromatography to yield bis(2,5-dioxopyrrolidin-l-yl) heptanedioate (ER-001236140) as a white solid (2.5 g, 71% yield). 1HNMR (400 MHz) δ ppm 2.83 (s, 8H), 2.64 (t, J = 7.6 Hz, 4H), 1.80 (dt, J= 7.6 Hz, 4H), 1.59-1.51 (m, 2H). LCMS (M+H)=355.2.
  • 2
  • [ 25528-46-5 ]
  • [ 74648-14-9 ]
  • Pimeloyl-Lys(Z)-OEt [ No CAS ]
  • 3
  • [ 74648-14-9 ]
  • [ 104-94-9 ]
  • [ 876760-85-9 ]
  • 4
  • [ 74648-14-9 ]
  • heptanedioic acid (4-methoxyphenyl)amide (2-oxotetrahydrofuran-3-yl)amide [ No CAS ]
  • 5
  • [ 6066-82-6 ]
  • [ 142-79-0 ]
  • [ 74648-14-9 ]
  • 6
  • [ 1096533-59-3 ]
  • [ 74648-14-9 ]
  • [ 1096533-30-0 ]
  • 7
  • [ 1609108-17-9 ]
  • [ 74648-14-9 ]
  • [ 1609108-16-8 ]
YieldReaction ConditionsOperation in experiment
34% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 0.583333h; Example A67 Preparation of Ar-{7-[(2,5-dioxopyrrolidin-l-yl)oxy]-7-oxoheptanoyl}-L-valyl-N-[4-([(2- [(3Λ,55,7Λ,8Λ)-7-{(1£,3^-5-[(25,35,5Λ,^ dimethyltetrahydro-2H-pyran-2-yl]-3-methylpenta-l,3-dien-l-yl}-8-hydroxy-l,6- dioxaspiro[2.5]oct-5-yl]acetyl}hydrazinyl)carbonyl]oxy}methyl)phenyl]-A^-carbamoyl-L- ornithinamide (B190). Step 1. Synthesis of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N-[4-( [(2- [(3R,5S,7R,8R)-7-{(l£,3£)-5-[(2S,3S,5R,6R)-5-[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}-3,6- dimethyltetrahydro-2H-pyran-2-yl]-3-methylpenta-l,3-dien-l -yl}-8-hydroxy-l,6-dioxaspiro[2.5]oct-5- yl]acetyl}hydrazinyl)carbonyl]oxy}methyl)phenyl]-N5-carbamoyl-L-ornithinamide (B191). To a solution of B6 (19.4 mg, 0.035 mmol, 1 eq.) in NN-dimethylformamide (0.5 mL) at rt was added NN-diisopropylethylamine (24.7 μL, 0.14 mmol, 4 eq.), 2,6-lutidine (16.3 μ^, 0.14 mmol, 4 eq.), 4- NN-dimethylamino pyridine (4.3 mg, 0.035 mmol, 1 eq.) and N-[(9H-fluoren-9-ylmethoxy)carbonyl]- L-valyl-N5-carbamoyl-N-[4-([(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide (40.6 mg, 0.053 mmol, 1.5 eq.), and the reaction was stirred for 2.5 h. More N-[(9H-fluoren-9- ylmethoxy)carbonyl]-L-valyl-N5-carbamoyl-N-[4-( [(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L- ornithinamide (13.5 mg, 0.018 mmol, 0.5 eq.) was added, and the reaction was stirred for another 1 h. The reaction was purified by reverse phase chromatography (Method A) to give B191 as a white solid. Yield: 9.4 mg, 0.0081 mmol, 23%. LCMS (Protocol D): m/z 1177.8 [M+H] , retention time = 0.90 minutes. Step 2. Synthesis of L-valyl-N-[4-( [(2-[(3R,5S,7R,8R)-7- {(l£',3£')-5-[(2S,3S,5R,6R)-5- [(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}-3,6-dimethyltetrahydro-2H-pyran-2-yl]-3-methylpenta- 1 ,3 -dien- 1 -yl } - 8 -hydroxy- 1 ,6-dioxaspiro [2.5 ] oct-5 - yl]acetyl}hydrazinyl)carbonyl]oxy}methyl)phenyl]-N5-carbamoyl-L-ornithinamide acetate salt (B192). The title compound was prepared in 56% yield from 9.4 mg (0.008 mmol, 1.0 eq) of B191 and 13.6 mg (0.16 mmol, 20.0 eq) of piperidine using the procedure described for preparation of compound B47. LCMS (Protocol D): m/z 955.8 [M+H]+, retention time = 0.65 minutes. Step 3. Synthesis of N-{7-[(2,5-dioxopyrrolidin-l-yl)oxy]-7-oxoheptanoyl}-L-valyl-N-[4- ([(2-[(3R,5S,7R,8R)-7-{(l£,3£)-5-[(2S,3S,5R,6R)-5- [(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}- 3,6-dimethyltetrahydro-2H-pyran-2-yl] -3 -methylpenta- 1 ,3-dien- 1 -yl} -8-hydroxy- 1 ,6- dioxaspiro [2.5] oct-5 -yl] acetyl} hydrazinyl)carbonyl] oxy } methyl)phenyl] -N5-carbamoyl-L- ornithinamide (B190). To a solution of B192 (4.5 mg, 0.004 mmol, 1 eq.) in NN- dimethylformamide (0.3 mL) at rt was added NN-diisopropylethylamine (3.5 μL, 0.02 mmol, 5 eq.) followed by l,l'-[(l,7-dioxoheptane-l,7-diyl)bis(oxy)]dipyrrolidine-2,5-dione (prepared as in J.Am.Chem.Soc. 2006, 128, 2802, 8.9 mg, 0.025 mmol) 6.2 eq.), and the reaction was allowed to stir for 35 min. The reaction was purified by reverse phase chromatography (Method A) to give B190 as a white solid. Yield: 1.65 mg, 0.0014 mmol, 34%. LCMS (Protocol D): m/z 1194.80 [M+H]+, retention time = 0.75 minutes. lH NMR (500 MHz, CD3CN) δ 9.06 (s, 1 H), 8.17 (s, 1 H), 7.71-7.63 (m, 2 H), 7.35-7.25 (m, 2 H), 7.19 (d, J= 7.6 Hz, 1 H), 6.73 (d, J= 6.6 Hz, 1 H), 6.47 (d, J= 8.8 Hz, 1 H), 6.41- 6.30 (m, 2 H), 5.96-5.85 (m, 2 H), 5.67-5.50 (m, 2 H), 5.33-5.24 (m, 1 H), 5.08-4.99 (m, 2 H), 4.74 (s, 1 H), 4.57-4.48 (m, 1 H), 4.39-4.25 (m, 2 H), 4.15-4.08 (m, 1 H), 3.82-3.75 (m, 1 H), 3.67-3.59 (m, 1 H), 3.55-3.47 (m, 1 H), 3.35-3.20 (m, 2 H), 3.12-2.99 (m, 2 H), 2.82-2.73 (m, 5 H), 2.66-2.52 (m, 6 H), 2.46-2.38 (m, 2 H), 2.36-2.20 (m, 4 H), 1.98 (s, 3 H), 1.77-1.57 (m, 11 H), 1.53-1.36 (m, 6 H), 1.30 (d, J= 6.6 Hz, 3 H), 1.06 (d, J= 6.6 Hz, 3 H), 1.00-0.91 (m, 9 H).
 

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