(2S)-2-amino-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpent-4-enamide

Base Information

• Chemical Name: (2S)-2-amino-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpent-4-enamide
• CAS No.: 225938-47-6
• Molecular Formula: C15H22 N2 O2
• Molecular Weight: 262.352
• DSSTox Substance ID: DTXSID60572718
• Nikkaji Number: J1.127.804C
• Wikidata: Q82461165
• Mol file: 225938-47-6.mol

Synonyms:225938-47-6;(2S)-2-amino-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpent-4-enamide;(2S)-AMINO-N-[(1R,2R)-2-HYDROXY-1-METHYL-2-PHENYLETHYL]-N-METHYL-4-PENTENAMIDE;DTXSID60572718

Chemical Property of (2S)-2-amino-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpent-4-enamide

Chemical Property:

• PSA: 66.56000
• LogP: 2.17060
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 262.168127949
• Heavy Atom Count: 19
• Complexity: 301

Purity/Quality:

97% ^*data from raw suppliers

(2S)-AMINO-N-[(1R,2R)-2-HYDROXY-1-METHYL-2-PHENYLETHYL]-N-METHYL-4-PENTENAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C1=CC=CC=C1)O)N(C)C(=O)C(CC=C)N
• Isomeric SMILES: C[C@H]([C@@H](C1=CC=CC=C1)O)N(C)C(=O)[C@H](CC=C)N

Technology Process of (2S)-2-amino-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpent-4-enamide

There total 3 articles about (2S)-2-amino-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpent-4-enamide 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: 71.0%

allyl bromide (106-95-6) + 2-amino-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylacetamide (170115-98-7) → <1R(S),2R>-N-(2-hydroxy-1-methyl-2-phenethyl)-2-amino-N-methyl-4-pentenamide (225938-47-6)

Guidance literature:

2-amino-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylacetamide; With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; at 0 - 5 ℃; for 1.25h; Inert atmosphere;

allyl bromide; In tetrahydrofuran; hexane; at 0 - 5 ℃; for 0.75h; Inert atmosphere;

DOI:10.15227/orgsyn.076.0057

Reference yield:

(1R,2R)-pseudoephedrine (321-97-1,7009-81-6,90-83-5,6912-63-6) → <1R(S),2R>-N-(2-hydroxy-1-methyl-2-phenethyl)-2-amino-N-methyl-4-pentenamide (225938-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiCl; LiHMDS / tetrahydrofuran

1.2: tetrahydrofuran

With lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1002/chem.200305421

Reference yield:

allyl bromide (106-95-6) + 2-amino-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylacetamide (170115-98-7) → (R)-2-Amino-pent-4-enoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide + <1R(S),2R>-N-(2-hydroxy-1-methyl-2-phenethyl)-2-amino-N-methyl-4-pentenamide (225938-47-6)

Guidance literature:

With lithium chloride; lithium hexamethyldisilazane; Yield given; Multistep reaction. Yields of byproduct given; 1.) THF, 0 deg C, 20 min, 2.) 0 deg C, 1 h;

DOI:10.1021/jo990341z

upstream raw materials:

allyl bromide

2-amino-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methylacetamide

(1R,2R)-pseudoephedrine

Downstream raw materials:

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-pentenoate

(E)-(S)-5-tert-Butoxycarbonylamino-hex-2-enedioic acid 6-benzyl ester 1-cyclohexyl ester

2-tert-butoxycarbonylamino-hexanedioic acid 6-cyclohexyl ester