85642-13-3

Basic information

• Product Name: BOC-ALA-NH2
• Synonyms: BOC-L-ALA-NH2;BOC-ALA-NH2;BOC-Beta-ala-NH2;N-alpha-t-Butyloxycarbonyl-beta-alanine amide;N-t-Butyloxycarbonyl-L-alanine amide;Boc-L-alanine amide;N-tert-Butoxycarbonyl-L-alanine amide;Boc-L-alanine-NH2
• CAS NO: 85642-13-3
• Molecular Formula: C₈H₁₆N₂O₃
• Molecular Weight: 188.22
• EINECS: 1533716-785-6
• Mol File: 85642-13-3.mol

Chemical Properties

• Melting Point: 124-125 °C
• Boiling Point: 343.1 °C at 760 mmHg
• Flash Point: 161.3 °C
• Appearance: /Solid
• Density: 1.081 g/cm³
• Vapor Pressure: 7.19E-05mmHg at 25°C
• Refractive Index: 1.463
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.38±0.46(Predicted)
• Water Solubility: Soluble in water or 1% acetic acid.
• CAS DataBase Reference: BOC-ALA-NH2(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-ALA-NH2(85642-13-3)
• EPA Substance Registry System: BOC-ALA-NH2(85642-13-3)

Safety Data

• Hazardous Substances Data: 85642-13-3(Hazardous Substances Data)

Usage

Uses

N-Boc-L-alaninamide is used as pharmaceutical intermediate.

InChI:InChI=1/C8H16N2O3/c1-5(6(9)11)10-7(12)13-8(2,3)4/h5H,1-4H3,(H2,9,11)(H,10,12)/t5-/m0/s1

Upstream product

• 15761-38-3 L-N-Boc-Ala 

Downstream Products

• 141041-80-7 N-(tert-Butyloxycarbonyl)-DL-alaninnitril 
• 657423-49-9 tert-butyl [2-amino-2-(hydroxyimino-1-methylethyl)]carbamate 
• 96929-01-0 N-(tert-Butyloxycarbonyl)-DL-thioalaninamid 
• 1357830-46-6 tert-butyl 1-(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethylcarbamate 
• 149632-73-5 dl-1-amino-2-(1,1-dimethylethoxy)carbonylamino-propane 
• 130013-83-1 (S)-2-(tert-butoxycarbonylamino)propanenitrile 
• 141041-86-3 tert-butyl (S)-(1-amino-1-thioxopropan-2-yl)carbamate 
• 927438-81-1 3-{[2-(1-tert-butoxycarbonylamino-ethyl)-thiazole-4-carbonyl]-amino}-2-methyl-hexanoic acid 1-benzyloxycarbonyl-ethyl ester 
• 927438-79-7 3-{[2-(1-tert-butoxycarbonylamino-ethyl)-thiazole-4-carbonyl]-amino}-2-methyl-hexanoic acid 1-({1-[(1-tert-butoxycarbonyl-2-methyl-propyl)-methyl-carbamoyl]-2-phenyl-ethyl}-methyl-carbamoyl)-ethyl ester 
• 205648-22-2 (S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxamide 
• 205648-23-3 (S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-thiocarboxamide 
• 205648-21-1 (S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxylic acid 
• 205648-20-0 (S)-ethyl 6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxylate 
• 205648-24-4 (S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}-3-(4-ethoxycarbonylthiazol-2-yl)pyridine 

Relevant articles and documents

Solid-Phase Total Synthesis of Yaku'amide B Enabled by Traceless Staudinger Ligation

We report a solid-phase strategy for total synthesis of the peptidic natural product yaku'amide B (1), which exhibits antiproliferative activity against various cancer cells. Its linear tridecapeptide sequence bears four β,β-dialkylated α,β-dehydroamino acid residues and is capped with an N-terminal acyl group (NTA) and a C-terminal amine (CTA). To realize the Fmoc-based solid-phase synthesis of this complex structure, we developed new methods for enamide formation, enamide deprotection, and C-terminal modification. First, traceless Staudinger ligation enabled enamide formation between sterically encumbered alkenyl azides and newly designed phosphinophenol esters. Second, application of Eu(OTf)3 led to chemoselective removal of the enamide Boc groups without detaching the resin linker. Finally, resin-cleavage and C-terminus modification were simultaneously achieved with an ester–amide exchange reaction using CTA and AlMe3 to deliver 1 in 9.1 % overall yield (24 steps from the resin).