McMMAE synthesis
- Product Name:McMMAE
- CAS Number:863971-24-8
- Molecular formula:C49H78N6O10
- Molecular Weight:911.18
55750-53-3
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Yield:863971-24-8 36%
Reaction Conditions:
with diethyl cyanophosphonate;N-ethyl-N,N-diisopropylamine in dichloromethane at 20; for 12 h;Inert atmosphere;
Steps:
15 Preparation of 6-Maleimidocaproyl-MMAE
To a suspension of MMAE (0.05 g, 0.0694 mmol) in freshly distilled dry DCM (2 ml), 6-maleimidocaproic acid (0.0221 g, 0.104 mmol) was added followed by diethylcyanophosphonate (21 μΙ, 0.139 mmol) and DIPEA (37 μΙ, 0.208 mmol). On addition of DIPEA, the reaction mixture became clear and was stirred at room temperature under nitrogen for 12 h, TLC [silica gel: 5% MeOH/DCM, Rf 0.31]. The reaction mixture was diluted with DCM (30 ml) and washed with 10% citric acid (2 X 20 ml), water (20 ml), brine (20 ml) and concentrated to dryness. The crude was purified by flash column chromatography [silica gel: 5% MeOH/DCM] to give 6- Maleimidocaproyl-MMAE 37 as a white solid 0.023 g (36%). MS (m/z) found 911.58 (M+1) calculated for C49H79N6O10
References:
WO2016/46574,2016,A1 Location in patent:Page/Page column 75
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