ChemicalBook CAS DataBase List MonoMethylauristatin F

MonoMethylauristatin F synthesis

12synthesis methods

Product Name:MonoMethylauristatin F
CAS Number:745017-94-1
Molecular formula:C39H65N5O8
Molecular Weight:731.96

L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-L-valyl-L-valyl-(3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino)heptanoyl-(αR,βR,2S)-β-methoxy-α-methyl-2-pyrrolidinepropanoyl-

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Yield:745017-94-1 100%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;water at 20; for 0.583333 h;

Steps:

40 Example 40. (S)-2-((2R,3R)-3-((S)- 1 -((3R,4S ,5S)-4-((S)-N,3-dimethyl-2-((S)-3- methyl-2-(methylamino)butanamido)butanamido)-3 -methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3 -methoxy-2-methylpropanamido)-3 -phenylpropanoic acid (101)

(S)-2-((2R,3R)-3-((S)- 1 -((6S ,9S, 12S, 1 3R)- 12-((S)-sec-butyl)-6,9-diisopropyl- 13- methoxy-2,2,5,11 -tetramethyl-4,7, 1 0-trioxo-3 -oxa-5 ,8,11 -triazapenta-decan- 15- oyl)pyrrolidin-2-yl)-3 -methoxy-2-methylpropanamido)-3 -phenylpropanoic acid (25 mg,0.030 mmol) in the mixture of HC1 (conc. 0.3 ml) and 1,4-dioxane (0.9 ml) was stirred at RT for 35 mm. The mixture was diluted with EtOH (1.0 ml) and toluene (1.0 ml), concentrated and re-evaporated with EtOH/toluene (2:1) to afford the title compound as a white solid (22 mg, -400% yield) for the next step without further purification. LC-MS (ESI) mlz calcd. for C39H66N508 [M+Hj: 732.48, found: 732.60.

References:

WO2015/155753,2015,A2 Location in patent:Page/Page column 101