(S)-Boc-2-amino-4,4,4-trifluoro-butyric acid

Base Information

• Chemical Name: (S)-Boc-2-amino-4,4,4-trifluoro-butyric acid
• CAS No.: 181128-25-6
• Molecular Formula: C9H14F3NO4
• Molecular Weight: 257.21
• Hs Code.: 2922498590
• European Community (EC) Number: 872-220-2
• Nikkaji Number: J1.487.766E
• Mol file: 181128-25-6.mol

Synonyms:181128-25-6;(S)-BOC-2-AMINO-4,4,4-TRIFLUORO-BUTYRIC ACID;(L)-4,4,4-Trifluoro-alpha-homoalanine, N-BOC protected;(S)-2-((tert-Butoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid;(2S)-4,4,4-trifluoro-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;Butanoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-4,4,4-trifluoro-, (2S)-;SCHEMBL1515640;(2S)-2-Amino-4,4,4-trifluorobutanoic acid, N-BOC protected;(2S)-2-[(tert-Butoxycarbonyl)amino]-4,4,4-trifluorobutanoic acid;MFCD08532484;AKOS027321397;CS-0226391;E78000;(R)-Boc-2-amino-4,4,4-trifluoro-butyric acid;EN300-1589936;(2S)-2-(tert-Butoxycarbonylamino)-4,4,4-trifluorobutyric acid;(S)-2-(tert-butoxycarbonylamino)-4,4,4-trifluorobutanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-4,4,4-trifluorobutanoicacid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-4,4,4-trifluorobutanoic acid

Chemical Property of (S)-Boc-2-amino-4,4,4-trifluoro-butyric acid

Chemical Property:

• Boiling Point: 322.8±42.0 °C(Predicted)
• PKA: 3.34±0.10(Predicted)
• PSA: 79.12000
• Density: 1.280±0.06 g/cm3(Predicted)
• LogP: 2.12110
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 257.08749241
• Heavy Atom Count: 17
• Complexity: 296

Purity/Quality:

99% ^*data from raw suppliers

(2S)-2-Amino-4,4,4-trifluorobutanoic acid, N-Boc protected ^*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(CC(F)(F)F)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC(F)(F)F)C(=O)O

Technology Process of (S)-Boc-2-amino-4,4,4-trifluoro-butyric acid

There total 4 articles about (S)-Boc-2-amino-4,4,4-trifluoro-butyric 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: 80.0%

1,1-dimethylethyl [(1S)-3,3,3-trifluoro-1-(hydroxymethyl)propyl]carbamate (610272-57-6) → (2S)-2-({[(1,1-dimethylethyl)oxyl]carbonyl}amino)-4,4,4-trifluorobutanoic acid (181128-25-6)

Guidance literature:

With jones reagent; In acetone; at 0 ℃;

DOI:10.1021/jo0344384

Reference yield:

(2S)-1-benzyloxy-2-(tert-butoxycarbonyl)amino-4,4,4-trifluorobutane (610272-56-5) → (2S)-2-({[(1,1-dimethylethyl)oxyl]carbonyl}amino)-4,4,4-trifluorobutanoic acid (181128-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / hydrogen / Pd(OH)2/C / tetrahydrofuran / 2 h

2: 80 percent / Jones reagent / acetone / 0 °C

With jones reagent; hydrogen; palladium dihydroxide; In tetrahydrofuran; acetone;

DOI:10.1021/jo0344384

Reference yield:

(2R,3R)-1-benzyloxy-2-(tert-butoxycarbonyl)amino-4,4,4-trifluorobutan-3-ol (610272-53-2) → (2S)-2-({[(1,1-dimethylethyl)oxyl]carbonyl}amino)-4,4,4-trifluorobutanoic acid (181128-25-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / DMAP; molecular sieves 4 Angstroem / toluene / 20 °C

2: 85 percent / Bu₃SnH; AIBN / toluene / 1 h / 80 °C

3: 99 percent / hydrogen / Pd(OH)2/C / tetrahydrofuran / 2 h

4: 80 percent / Jones reagent / acetone / 0 °C

With dmap; jones reagent; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; hydrogen; tri-n-butyl-tin hydride; palladium dihydroxide; In tetrahydrofuran; acetone; toluene;

DOI:10.1021/jo0344384

upstream raw materials:

1,1-dimethylethyl [(1S)-3,3,3-trifluoro-1-(hydroxymethyl)propyl]carbamate

(2S)-1-benzyloxy-2-(tert-butoxycarbonyl)amino-4,4,4-trifluorobutane

(2R,3R)-1-benzyloxy-2-(tert-butoxycarbonyl)amino-4,4,4-trifluorobutan-3-ol

thiocarbonic acid O-(3-benzyloxy-2-tert-butoxycarbonylamino-1-trifluoromethyl-propyl) ester O-phenyl ester

Refernces

• 1、 Jiang, Zhong-Xing,Qin, Ying-Ying,Qing, Feng-Ling. "Asymmetric synthesis of both enantiomers of anti-4,4,4-trifluorothreonine and 2-amino-4,4,4-trifluorobutanoic acid". . p. 7544 - 7547. Retrieved 2007/10/03.