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ChemicalBook CAS DataBase List (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid
1012341-50-2

(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid synthesis

5synthesis methods
(2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid is a key intermediate in the preparation of Sacubitril. It can be synthesized by reacting (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoic acid with di-tert-butyl dicarbonate.
1012341-48-8 Synthesis
(R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid

1012341-48-8
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Yield:1012341-50-2 91.9%

Reaction Conditions:

with ammonium formate;nickel(II) acetate tetrahydrate;(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine in ethanol at 55; for 8 h;Temperature;

Steps:

1-9 Example 9The compound (2R, 4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid of this example is prepared as follows
Under an atmosphere of air, place the compound of formula II (E)-(R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid in a clean reaction flask 38.1g (0.1 mol),Nickel acetate tetrahydrate 373.5mg (1.5mmol),(R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine 815mg (1.5mmol) and ammonium formate 37.8g ( 0.6mol) dissolved in 500mL ethanol solvent, stirred and mixed well, and heated up,The mixture was stirred at 55° C. for an asymmetric reduction reaction for 8 hours,After the reaction, ethanol was removed by distillation under reduced pressure,To the residue, add 30 g of diatomaceous earth and 300 mL of isopropyl acetate,After stirring for 1 hour and filtering, the resulting filtrate was heated to reflux,800 mL of n-heptane was added dropwise within 2 hours, and then slowly cooled to room temperature,When the cooling rate is 5/hour, a large number of crystals are precipitated.The resulting crystals were filtered and dried under vacuum at 40°C,The compound of formula I is obtained as a white solid product(2R, 4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid 35.1g,The yield was 91.9%.

References:

Taizhou Polytechnic College;Zhou Liping;Chen Yunhua;Ye Haiwei;Jiang Ying;Lu Congling;Hu Meijie CN111269148, 2020, A Location in patent:Paragraph 0033-0061

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