(R)-tert-Butyl (1-phenylbut-3-en-2-yl)carbamate

Base Information

• Chemical Name: (R)-tert-Butyl (1-phenylbut-3-en-2-yl)carbamate
• CAS No.: 244092-76-0
• Molecular Formula: C15H21 N O2
• Molecular Weight: 247.337
• DSSTox Substance ID: DTXSID60445115
• Nikkaji Number: J1.349.364B
• Wikidata: Q82263451
• Mol file: 244092-76-0.mol

Synonyms:244092-76-0;(R)-tert-Butyl (1-phenylbut-3-en-2-yl)carbamate;(R)-tert-Butyl(1-phenylbut-3-en-2-yl)carbamate;TERT-BUTYL N-[(2R)-1-PHENYLBUT-3-EN-2-YL]CARBAMATE;3R enantiomer;N-[(1R)-1-(Phenylmethyl)-2-propen-1-yl]carbamic Acid 1,1-Dimethylethyl Ester;SCHEMBL13937947;DTXSID60445115;AKOS015890951;CS-0162445;D85963;(R)-tert-butyl 1-phenylbut-3-en-2-ylcarbamate;tert-butyl (R)-(1-phenylbut-3-en-2-yl)carbamate;(R)-3-(tert-Butoxycarbonylamino)-4-phenyl-1-butene

Chemical Property of (R)-tert-Butyl (1-phenylbut-3-en-2-yl)carbamate

Chemical Property:

• Melting Point: 67-68 °C
• Boiling Point: 361.9±31.0 °C(Predicted)
• PKA: 12.07±0.46(Predicted)
• PSA: 41.82000
• Density: 1.006±0.06 g/cm3(Predicted)
• LogP: 3.51280
• Storage Temp.: 2-8°C
• Solubility.: Chloroform
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 247.157228913
• Heavy Atom Count: 18
• Complexity: 275

Purity/Quality:

98% ^*data from raw suppliers

N-[(1R)-1-(Phenylmethyl)-2-propen-1-yl]carbamicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C=C
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=CC=C1)C=C
• Uses: N-[(1R)-1-(Phenylmethyl)-2-propen-1-yl]carbamic Acid 1,1-Dimethylethyl Ester is an intermediate used in the synthesis of N-protected α-amino epoxids, key intermediates for HIV protease inhibitors.

Technology Process of (R)-tert-Butyl (1-phenylbut-3-en-2-yl)carbamate

There total 5 articles about (R)-tert-Butyl (1-phenylbut-3-en-2-yl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-1-benzyl-prop-2-enylamine (756462-76-7) → (R)-N-(tert-butoxycarbonyl)-3-amino-4-phenyl-1-butene (244092-76-0)

Guidance literature:

With triethylamine; In dichloromethane; for 29h;

DOI:10.1021/op100174j

Reference yield:

Methyltriphenylphosphonium bromide (1779-49-3) + N-(tert-butoxycarbonyl)-D-phenylalaninal (77119-85-8) → (R)-N-(tert-butoxycarbonyl)-3-amino-4-phenyl-1-butene (244092-76-0)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dimethyl sulfoxide; at 0 ℃; for 1h;

N-(tert-butoxycarbonyl)-D-phenylalaninal; In tetrahydrofuran; dimethyl sulfoxide; at -78 - 45 ℃; for 16h;

DOI:10.1021/jm049566e

Reference yield:

Boc-D-Phe-OH (18942-49-9) → (R)-N-(tert-butoxycarbonyl)-3-amino-4-phenyl-1-butene (244092-76-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Inert atmosphere

1.2: Inert atmosphere

2.1: lithium aluminium tetrahydride / Inert atmosphere

3.1: Acidic conditions; Inert atmosphere

3.2: Inert atmosphere

With lithium aluminium tetrahydride;

DOI:10.1021/acs.jmedchem.6b01482

upstream raw materials:

Methyltriphenylphosphonium bromide

N-(tert-butoxycarbonyl)-D-phenylalaninal

di-tert-butyl dicarbonate

(R)-1-benzyl-prop-2-enylamine

Downstream raw materials:

((S)-1-benzylallyl)carbamic acid tert-butyl ester

(S)-1-phenylbut-3-en-2-amine

1(R,S)-<1'-(S)-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>oxirane

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

Refernces

• 1、 Velmourougane, Geetha,Harbut, Michael B.,Dalal, Seema,McGowan, Sheena,Oellig, Christine A.,Meinhardt, Nataline,Whisstock, James C.,Klemba, Michael,Greenbaum, Doron C.. "Synthesis of new (-)-bestatin-based inhibitor libraries reveals a novel binding mode in the S1 pocket of the essential malaria M1 metalloaminopeptidase". experimental part. p. 1655 - 1666. Retrieved 2011/05/16.
• 2、 Bakshi, Pancham,Wolfe, Michael S.. "Stereochemical analysis of (hydroxyethyl)urea peptidomimetic inhibitors of γ-secretase". . p. 6485 - 6489. Retrieved 2007/10/03.