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 
• 1431556-38-5 C₁₆H₂₃NO₇S 
• 100-59-4 phenylmagnesium chloride 
• 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 
• 3218-36-8 4-Phenylbenzaldehyde 

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 
• 149709-62-6 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 
• 149709-59-1 (R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid ethyl ester 

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.

Method for synthesizing AHU377 calcium salt

The invention discloses a method for synthesizing an AHU377 calcium salt. The method comprises the following steps: reacting 4-bromo-D-phenylalanine with thionyl chloride, reacting obtained methyl 4-bromo-D-phenylalaninate hydrochloride with BOC acid anhydride, reacting the obtained reaction product with phenylmagnesium bromide to obtain N-tert-butyloxycarbonyl-amino-4,4-biphenyl-R-alanine methylester, reacting the N-tert-butyloxycarbonyl-amino-4,4-biphenyl-R-alanine methyl ester with sodium borohydride, reacting the obtained reaction product with ethyl 2-(triphenylphosphoranylidene)propionate to obtain ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[tert-butoxycarbonyl]amino]-2-methyl-2-pentenoate, reacting the ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[tert-butoxycarbonyl]amino]-2-methyl-2-pentenoatewith lithium hydroxide, performing catalytic hydrogenation, reacting the obtained catalytic hydrogenation product with thionyl chloride to obtain ethyl (2R, 4S)-5- ([1,1-biphenyl)-4-amino-2-methylpentenoate hydrochloride, and stirring and reacting the ethyl (2R, 4S)-5- ([1,1-biphenyl)-4-amino-2-methylpentenoate hydrochloride, calcium chloride and succinic anhydride to obtain the target product.The method has the advantages of simple steps, mild reaction conditions, high purity and high yield.

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.