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Chemical Structure| 663921-15-1 Chemical Structure| 663921-15-1
Chemical Structure| 663921-15-1

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CAS No.: 663921-15-1

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NH2-PEG4-CH2CH2COOH is a cleavable 4 unit PEG ADC linker used in the synthesis of antibody-drug conjugates (ADCs).

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Product Details of NH2-PEG4-CH2CH2COOH

CAS No. :663921-15-1
Formula : C11H23NO6
M.W : 265.30
SMILES Code : O=C(O)CCOCCOCCOCCOCCN
MDL No. :MFCD11041129
InChI Key :DKUZHSDZSMQOGQ-UHFFFAOYSA-N
Pubchem ID :22731902

Safety of NH2-PEG4-CH2CH2COOH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of NH2-PEG4-CH2CH2COOH

* 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 [ 663921-15-1 ]

[ 663921-15-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 39028-27-8 ]
  • [ 663921-15-1 ]
  • [ 18107-18-1 ]
  • [ 1268593-67-4 ]
YieldReaction ConditionsOperation in experiment
2.5. Methyl 3-[2-(2-{2-[2-(2-iodoacetylamino)ethoxy]ethoxy}ethoxy)ethoxy]propanoate 117.4 mg of N-hydroxysuccinimidyl iodoacetate in solution in 3 ml of DCM are added to 100 mg of 3-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)propanoic acid. After 2 h at AT, 330 mul of MeOH are added and the mixture is cooled to 0 C. 360 mul of a 2M solution of trimethylsilyldiazomethane in hexane are added. After 1 h, the mixture is neutralized by addition of 50 mul of acetic acid and then a saturated aqueous NaHCO3 solution is added until pH=8 is obtained. The organic phase is dried over MgSO4 and concentrated under RP, and the residue is purified by flash chromatography on silica (Interchrom Puriflash Silica 15/35U 10G) using a gradient from 0 to 10% of methanol in DCM. 132 mg of methyl 3-[2-(2-{2-[2-(2-iodoacetylamino)ethoxy]ethoxy}ethoxy)ethoxy]propanoate are thus obtained. 1H NMR (400 MHz, d6-DMSO): 2.54 (t, J=6.4 Hz, 2H); 3.20 (q, J=5.8 Hz, 2H); 3.41 (t, J=5.8 Hz, 2H); 3.48 to 3.53 (m, 12H); 3.60 (s, 3H); 3.63 (t, J=6.4 Hz, 2H); 3.65 (s, 2H); 8.27 (broad t, J=5.8 Hz, 1H). LC/MS (A): rt=0.54 min; [M+H]+: m/z 448; [M+HCO2H-H]-: m/z 492.
  • 2
  • [ 6066-82-6 ]
  • [ 663921-15-1 ]
  • [ 1426827-79-3 ]
  • 2,5-dioxopyrrolidin-1-yl 1-[({endo-bicyclo[6.1.0]non-4-yn-9-ylmethoxy}carbonyl)amino]-3,6,9,12-tetraoxapentadecan-15-oate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% To a solution of amino-dPEG4-acid (1.23 g, 4.23 mmol) in anhydrous DMF (30 mL)were subsequently added 51 (1.02 g, 3.85 mmol) and triethylamine (1.60 mL, 11.53mmol). The reaction mixture was stirred for 3h at rt, after which EDCI.HC1 (0.884 g,4.61 mmol) and NHS (88 mg, 0.77 mmol) were added. The resulting solution was stirredovernight at rt and poured into 100 mL NaHCO3 (sat.) and 150 mL EtOAc. The layerswere separated and the organic phase was washed with sat. NaHCO3 (90 mL) and H20 (75 mL). The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. Gradient flash chromatography (MeCN -* MeCN:H20 30:1) afforded product 60a as colorless oil (800 mg, 1.48 mmol, 40%).
  • 3
  • [ 663921-15-1 ]
  • [ 55750-62-4 ]
  • [ 1263045-16-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 20℃; for 2h; Compound 3-11 (4.55 g, 18.7 mmol) was dissolved in 10 mL water, NaHCO3 (1.71 g, 20.4 mmol) was added and the mixture was stirred. CE-L-055 (4.55 g, 17 mmol) in 30 mL 1,2-dimethoxyethane was added dropwise slowly. The reaction mixture was stirred for 2 hours at room temperature. 50 mL water was added, the mixture was adjusted to pH 3-4 with 1 M dilute hydrochloric acid, and then extracted with EtOAc for 10 times (50 mL×10). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to give the crude product, which was used directly for the next step. LCMS (ESI) m/z 417.2 (M+H)+.
 

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