4434-61-1

Basic information

• Product Name: N-CARBOBENZOXY-DL-METHIONINE
• Synonyms: Z-DL-METHIONINE;Z-DL-MET-OH;CBZ-DL-MET-OH;2-BENZYLOXYCARBONYLAMINO-4-METHYLSULFANYL-BUTYRIC ACID;Carbobenzoxymethionine;N-benzyloxycarbonyl-DL-methionine;N-CBZ-DL-Methionine N-Carbobenzyloxy-DL-methionine;Z-DL-MET
• CAS NO: 4434-61-1
• Molecular Formula: C₁₃H₁₇NO₄S
• Molecular Weight: 283.34
• EINECS: 224-640-7
• Product Categories: Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids
• Mol File: 4434-61-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 113 °C
• Boiling Point: 504.7 °C at 760 mmHg
• Flash Point: 259 °C
• Appearance: /
• Density: 1.253 g/cm³
• Vapor Pressure: 6.58E-14mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: -20°C
• Solubility: almost transparency in Methanol
• CAS DataBase Reference: N-CARBOBENZOXY-DL-METHIONINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOBENZOXY-DL-METHIONINE(4434-61-1)
• EPA Substance Registry System: N-CARBOBENZOXY-DL-METHIONINE(4434-61-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 4434-61-1(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline

InChI:InChI=1/C13H17NO4S/c1-9(16)14-11(13(17)18)8-19-12(7-15)10-5-3-2-4-6-10/h2-6,11-12,15H,7-8H2,1H3,(H,14,16)(H,17,18)/t11-,12?/m0/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 59-51-8 DL-methionine 
• 348-67-4 D-methionine 
• 921-01-7 rac-cysteine 
• 62-53-3 aniline 
• 127862-75-3 2-Benzyloxycarbonylamino-4-methylsulfanyl-butyric acid 2,2,2-trifluoro-ethyl ester 
• 64-17-5 ethanol 
• 16874-01-4 Z-Met-O-tBu 

Downstream Products

• 1152-62-1 (2R)-2-[[(benzyloxy)carbonyl]amino]-4-(methylsulfanyl)butanoic acid 
• 95277-61-5 (S)-benzyl 4-(methylthio)-1-oxo-1-(phenylamino)butan-2-ylcarbamate 
• 113718-97-1 L-Z-Met-OEt 
• 121335-14-6 2-Benzyloxycarbonylamino-4-methylsulfanyl-butyric acid 6-nitro-benzotriazol-1-yl ester 
• 1152-62-1 Cbz-Met-OH 
• 87023-92-5 N-benzyloxycarbonyl-DL-methionyl-(3,5-dimethyl)pyrazole 
• 102988-97-6 C₁₈H₂₅NO₆S 
• 245107-59-9 benzyl (2R,4R)-2-tert-butyl-4-[2-(methylthio)ethyl]-5-oxo-1,3-oxazolidine-3-carboxylate 
• 478647-31-3 tert-butyl N-[(benzyloxy)carbonyl]-L-methionyl-L-alaninate 

Relevant articles and documents

Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin

Enantioselective inclusion of α-amino acids with crystals of α-cyclodextrin (α-CD) has been achieved by converting the amino acids into sulfonate salts with pyrene-1-sulfonic acid (PyS). For example, crystals of α-CD selectively include L-leucine/PyS (1:1) salt in a host/guest ratio of ～1 with 92%ee from a solution of the racemic salt in ethanol/N-methylformamide (91:9) at 40 °C. Under conditions optimized for individual amino acids, the PyS salts of valine, phenylalanine, and methionine are also included with good enantioselectivities (up to 86%ee). Mechanistic studies for the inclusion of leucine/PyS salt reveals that the enantioselectivity originates from the difference in stability between the inclusion complexes of D- and L-leucine/PyS salts with α-CD in crystals.

POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS

The present invention relates to compounds of Formula (I) and pharmaceutically acceptable compositions thereof, useful as toll-like receptor 7/8 (TLR7/8) antagonists. In Formula (I), Ring A is aryl or heteroaryl; Ring B is aryl or heteroary; and X is C(R4)2, O, NR4, S, S(R4), or S(R4)2.

Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones

Routes to putative N-acyl-D-ala-D-ala surrogates, beginning with the conversion of 4-, 5-, and 6-membered lactones into 5-, 6-, and 7-membered cyclic hydroxamates, are reported. The key step of the synthesis is trimethylaluminium-promoted cyclization of an ω-aminooxyester. The 7-membered cyclic hydroxamate crystallizes in a chair conformation. Extension of the reaction sequence to homoserine or homoserine lactone leads to cyclocanaline and N-acylated cyclocanalines. The 4-phenylacetamido derivative of cyclocanaline crystallizes in a boat conformation. The attachment of a 2-carboxypropyl substituent to the ring nitrogen of a 4-acylaminocyclocanaline has been effected, prior to cyclization, by coupling of the acyclic aminooxyester precursor to the triflate of benzyl lactate or, after cyclization, by coupling to tert-butyl α-bromopropionate in the presence of potassium fluoride - alumina, followed by removal of the protecting group in each case. A six-membered homolog of the antibiotic lactivicin has been synthesized by the reaction of 4-phenylacetamidocyclocanaline with benzyl 2-oxoglutarate in the presence of carbodiimide, followed by hydrogenolysis. Starting with methyl 2,4-dibromo-2,4-dideoxy-L-erythronate, which is available in two steps from L-ascorbic acid, these reaction sequences have been applied to the stereospecific synthesis of a D-alanine derivative whose nitrogen atom is enclosed within a 3,4-disubstituted [1,2]oxazinan-3-one.