149818-98-4

Basic information

• Product Name: METHYL-N-TERT-BUTYLOXYCARBONYL-AMINO-4,4'-BIPHENYL-R-ALANINE
• Synonyms: METHYL-N-TERT-BUTYLOXYCARBONYL-AMINO-4,4'-BIPHENYL-R-ALANINE;methyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylphenyl)propanoate
• CAS NO: 149818-98-4
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.43
• Mol File: 149818-98-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 508.646°C at 760 mmHg
• Flash Point: 261.42°C
• Appearance: /
• Density: 1.113g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.538
• PKA: 10.95±0.46(Predicted)
• CAS DataBase Reference: METHYL-N-TERT-BUTYLOXYCARBONYL-AMINO-4,4'-BIPHENYL-R-ALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-N-TERT-BUTYLOXYCARBONYL-AMINO-4,4'-BIPHENYL-R-ALANINE(149818-98-4)
• EPA Substance Registry System: METHYL-N-TERT-BUTYLOXYCARBONYL-AMINO-4,4'-BIPHENYL-R-ALANINE(149818-98-4)

Safety Data

• Hazardous Substances Data: 149818-98-4(Hazardous Substances Data)

Usage

General Description

Methyl-N-tert-butyloxycarbonyl-amino-4,4'-biphenyl-R-alanine is a compound used in the field of organic chemistry as a building block for the synthesis of peptides and proteins. It is a derivative of alanine, an essential amino acid, with a methyl group and a tert-butyloxycarbonyl (Boc) protecting group attached to the nitrogen atom. The biphenyl group in the molecule provides steric hindrance, making it useful in the preparation of certain peptide structures. Overall, this chemical plays a crucial role in the development of new pharmaceuticals, as well as in the study of protein structure and function.

InChI:InChI=1/C21H25NO4/c1-21(2,3)26-20(24)22-18(19(23)25-4)14-15-10-12-17(13-11-15)16-8-6-5-7-9-16/h5-13,18H,14H2,1-4H3,(H,22,24)/t18-/m1/s1

Upstream product

• 123795-38-0 methyl (R)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propanoate 
• 100-63-0 phenylhydrazine 
• 1213855-60-7 methyl (R)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 62561-74-4 (2R)-2-amino-3-(4-bromophenyl)propanoic acid 
• 459133-43-8 (R)-2-amino-3-(4-bromophenyl)propionic acid methyl ester hydrochloride 
• 100-58-3 phenylmagnesium bromide 
• 91853-46-2 3-([1,1'-biphenyl]-4-yl)-2-oxopropanoic acid 
• 1188995-14-3 (Z)-4-([1,10-biphenyl]-4-ylmethylene)-2-methyloxazol-5(4H)-one 
• 1057002-37-5 4-[1-biphenyl-4-yl-meth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 98-80-6 phenylboronic acid 
• 99334-26-6 methyl (4-bromophenyl)pyruvate 
• 6362-58-9 methyl phenylpyruvate 
• 1589-82-8 phenylmagnesium bromide 

Downstream Products

• 149709-60-4 ethyl (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoate 
• 149690-12-0 (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride 
• 149709-59-1 ethyl 5-(4-<1,1'-biphenyl>yl)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-methyl-2-pentenoate 
• 1426129-50-1 N-[(1R)-2-[1,1'-biphenyl]-4-yl-1-(hydroxymethyl)ethyl]carbamic acid tert-butyl ester 
• 1012341-48-8 (2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid 
• 1012341-50-2 (2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid 
• 149709-59-1 (R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid ethyl ester 
• 149709-62-6 α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 149709-63-7 α-ethyl (αS,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 149709-63-7 α-ethyl (γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 149709-58-0 (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanal 
• 753421-85-1 ethyl (γS)-γ-amino-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 128779-47-5 (2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid 

Relevant articles and documents

Preparation method of sacubitril intermediate

The invention relates to the technical field of synthesis of medical intermediates, in particular to a preparation method of a sacubitril intermediate, which comprises the following steps: 1) reacting a raw material compound III with phosphorus trihalide to obtain a compound II; and 2) reacting the compound II with phenylhydrazine in the presence of a catalyst and an additive to obtain a sacubitril intermediate, namely a compound I. According to the invention, cheap phosphorus trihalide is selected to replace expensive and highly toxic trifluoromethanesulfonic anhydride, and cheap phenylhydrazine and a catalyst palladium chloride are adopted. The method has the advantages of simple reaction operation, low cost and high yield, and is easier for industrial production of the compound I.

Synthesis method of LCZ696 midbody

The invention discloses a synthesis method of an LCZ696 midbody (R)-tertiary butyl (1-([1,1'-biphenyl]-4-base)-3-hydroxyl propane-2-base) carbamic acid ester. The preparation method comprises the following steps that (1) a raw material BOC-D-tyrosine I reacts with substituent sulfonyl chloride to obtain a midbody II; (2) the midbody II and a phenyl Grignard reagent are subjected to coupling to obtain a midbody III; and (3) the midbody III is reduced through potassium borohydride to obtain (R)-tertiary butyl (1-([1,1'-biphenyl]-4-base)-3-hydroxyl propane-2-base) carbamic acid ester IV. The synthesis method utilizes cheap n-tosyl-l-alanyloxyindole to replace expensive and virulent trifluoromethanesulfonic acid, and meanwhile avoids to use the expensive metal catalyst Pd, the experiment is easy to operate, the yield is high, and the LCZ696 midbody is suitable for large-scale production.

R - biphenyl c serinol preparation method (by machine translation)

The invention relates to a preparation method for the intermediate sha kubi tune, in particular to a R - biphenyl c serinol preparation method, steps are as follows: first of all in order to D - tyrosine derivatives as raw materials with different substituted base sulfonic acid chloride (or anhydride) reaction, a compound represented by formula III, the compounds of the formula III are prepared through two routes the third ammonia is mellow R - biphenyl. Route a: type III of a compound represented by formula II shown in the reduction of the compound, then obtained by coupling the third ammonia is mellow R - biphenyl; line II: type III as shown in the coupling shown in formula V compound, further reduction to obtain R - biphenyl the third ammonia is mellow. Prepared by the method of the aforesaid compound R - biphenyl c sphingosine is model antihypertensive medicine LCZ696 (Entresto) of pegvisomant Sacubitril (AHU - 377) key intermediate. The method is simple in operation, short route, is suitable for industrial production. (by machine translation)