Butanamide, 2-amino-3,3-dimethyl-N-phenyl-, (2S)-

Base Information

• Chemical Name: Butanamide, 2-amino-3,3-dimethyl-N-phenyl-, (2S)-
• CAS No.: 171764-05-9
• Molecular Formula: C12H18N2O
• Molecular Weight: 206.288
• DSSTox Substance ID: DTXSID60449254
• Nikkaji Number: J3.302.364B
• Wikidata: Q82268666
• Mol file: 171764-05-9.mol

Synonyms:Butanamide, 2-amino-3,3-dimethyl-N-phenyl-, (2S)-;171764-05-9;(2S)-2-amino-3,3-dimethyl-N-phenylbutanamide;SCHEMBL8396733;DTXSID60449254;(2S)-N-Phenyl-2-amino-3,3-dimethylbutanamide

Chemical Property of Butanamide, 2-amino-3,3-dimethyl-N-phenyl-, (2S)-

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 206.141913202
• Heavy Atom Count: 15
• Complexity: 214

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(C(=O)NC1=CC=CC=C1)N
• Isomeric SMILES: CC(C)(C)[C@@H](C(=O)NC1=CC=CC=C1)N

Technology Process of Butanamide, 2-amino-3,3-dimethyl-N-phenyl-, (2S)-

There total 5 articles about Butanamide, 2-amino-3,3-dimethyl-N-phenyl-, (2S)- 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:

N-tert-butyloxycarbonyl-L-tert-leucine (62965-35-9) → (S)-tert-butylglycine phenylamide (171764-05-9)

Guidance literature:

Multi-step reaction with 2 steps

1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 25 °C

2: trifluoroacetic acid / dichloromethane / 2 h / 25 °C

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1002/jhet.4443

Reference yield:

(S)-tert-butyl 3,3-dimethyl-1-oxo-1-(phenylamino)butan-2-ylcarbamate (179533-91-6) → (S)-tert-butylglycine phenylamide (171764-05-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1002/jhet.4443

Reference yield:

(RS)-tert-leucine anilide (1454610-90-2) → (R)-tert-leucine anilide + (S)-tert-butylglycine phenylamide (171764-05-9)

Guidance literature:

With (S)-valine anilide imprinted poly(ethylene glycol dimethacrylate-co-methacrylic acid); In dichloromethane; at 24 ℃; for 2h; Optical yield = 9 %ee; Resolution of racemate;

DOI:10.1248/cpb.c12-01044

upstream raw materials:

(RS)-tert-leucine anilide

N-tert-butyloxycarbonyl-L-tert-leucine

aniline

(S)-tert-butyl 3,3-dimethyl-1-oxo-1-(phenylamino)butan-2-ylcarbamate

Downstream raw materials:

5-benzyloxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide

5-hydroxy-4(S)-methyl-2(R)-[2-(4-n-propylphenyl)ethyl]pentanoic acid 1-[(S)-tert-butylglycine phenylamide] amide

Refernces

• 1、 Dixon, Darren J.,Formica, Michele,Hamlin, Trevor A.,Rozsar, Daniel,Yamazaki, Ken. "Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides". . p. 1006 - 1015. Retrieved 2022/02/03.
• 2、 -. "Metalloproteinase inhibitors". . . Retrieved 2008/06/13.