(S)-2-(Tert-butoxycarbonylamino)-4,4-difluorobutanoic acid

Base Information

• Chemical Name: (S)-2-(Tert-butoxycarbonylamino)-4,4-difluorobutanoic acid
• CAS No.: 467442-20-2
• Molecular Formula: C9H15F2NO4
• Molecular Weight: 239.219
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID80692982
• Nikkaji Number: J2.043.654I
• Wikidata: Q72509766
• Mol file: 467442-20-2.mol

Synonyms:467442-20-2;(S)-2-(TERT-BUTOXYCARBONYLAMINO)-4,4-DIFLUOROBUTANOIC ACID;(2S)-4,4-difluoro-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-4,4-difluorobutanoic acid;DTXSID80692982;UCCLBCNDXKDPDT-YFKPBYRVSA-N;AMY15551;MFCD12755805;AKOS022177266;BS-49425;A7245;CS-0134029;F73118;(S)-2-(tert-butoxycarbonyl)-4,4-difluorobutanoic acid;(2S)-2-(tert-Butoxycarbonylamino)-4,4-difluorobutanoic acid;(S)-Boc-2-amino-4,4-difluoro-butyric acid (Boc-L-DfAbu-OH);(2S)-2-{[(tert-butoxy)carbonyl]amino}-4,4-difluorobutanoic acid;(2S)-2-[(TERT-BUTOXYCARBONYL)AMINO]-4,4-DIFLUOROBUTANOIC ACID

Chemical Property of (S)-2-(Tert-butoxycarbonylamino)-4,4-difluorobutanoic acid

Chemical Property:

• Vapor Pressure: 8.96E-06mmHg at 25°C
• Refractive Index: 1.433
• Boiling Point: 348.1 °C at 760 mmHg
• PKA: 3.48±0.10(Predicted)
• Flash Point: 164.3 °C
• PSA: 75.63000
• Density: 1.222 g/cm³
• LogP: 2.01040
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 239.09691428
• Heavy Atom Count: 16
• Complexity: 263

Purity/Quality:

95% purity ^*data from raw suppliers

Boc-L-DfAbu-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of (S)-2-(Tert-butoxycarbonylamino)-4,4-difluorobutanoic acid

There total 1 articles about (S)-2-(Tert-butoxycarbonylamino)-4,4-difluorobutanoic acid 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:

di-tert-butyl dicarbonate (24424-99-5) + α-amino-γ,γ-difluorobutyrate (121960-22-3) → 2-[(tert-butoxycarbonyl)amino]-4,4-difluorobutanoic acid (467442-20-2)

Guidance literature:

With triethylamine;

DOI:10.1016/j.bmcl.2003.09.084

Reference yield: 47.0%

2-[(tert-butoxycarbonyl)amino]-4,4-difluorobutanoic acid (467442-20-2) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 2-[(tert-butoxycarbonyl)amino]-4,4-difluorobutanoate (669083-19-6)

Guidance literature:

In methanol; toluene; at 0 ℃; for 3h; Sealed tube; Inert atmosphere;

DOI:10.1021/jm5018169

Reference yield:

2-[(tert-butoxycarbonyl)amino]-4,4-difluorobutanoic acid (467442-20-2) → {(S)-1-[(S)-1-((1S,2S,4R)-1-Benzyl-2-hydroxy-4-{(S)-2-methyl-1-[(pyridin-4-ylmethyl)-carbamoyl]-propylcarbamoyl}-pentylcarbamoyl)-ethylcarbamoyl]-3,3-difluoro-propyl}-carbamic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: PyBOP; i-Pr₂NEt / CH₂Cl₂

2: aq. NaOH / methanol

3: HOAt; EDCI; i-Pr₂NEt / tetrahydrofuran

With sodium hydroxide; 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.bmcl.2003.09.084

upstream raw materials:

di-tert-butyl dicarbonate

α-amino-γ,γ-difluorobutyrate

Downstream raw materials:

methyl 2-[(tert-butoxycarbonyl)amino]-4,4-difluorobutanoate

Refernces