(S)-3-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acid

Base Information

• Chemical Name: (S)-3-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acid
• CAS No.: 190897-47-3
• Molecular Formula: C9H17NO4
• Molecular Weight: 203.238
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID20476389
• Nikkaji Number: J1.191.867K
• Wikidata: Q72448260
• Mol file: 190897-47-3.mol

Synonyms:190897-47-3;(S)-3-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acid;(S)-3-(Boc-amino)-2-methylpropionic acid;BOC-S-3-AMINOISOBUTYRIC ACID;BOC-(S)-3-AMINO-2-METHYLPROPANOIC ACID;(2S)-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(2S)-3-{[(tert-butoxy)carbonyl]amino}-2-methylpropanoic acid;Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-, (2S)-;(S)-3-TERT-BUTOXYCARBONYLAMINO-2-METHYL-PROPIONIC ACID;MFCD04040045;(S)-Boc-beta2-Homoala-OH;SCHEMBL4740872;DTXSID20476389;(S)-N-T-BUTYLOXYCARBONYL-3-AMINO-2-METHYL PROPIONIC ACID;AKOS015893066;CS-W015457;GS-0809;F11549;EN300-3222127;(S)-3-(BOC-AMINO)-2-METHYLPROPANOIC ACID;A880395;(S)-3-((tert-Butoxycarbonyl)amino)-2-methylpropanoicacid;(2S)-3-[(tert-Butoxycarbonyl)amino]-2-methylpropanoic acid;(S)-3-(Boc-amino)-2-methylpropionic acid, >=98.0% (TLC)

Chemical Property of (S)-3-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acid

Chemical Property:

• Vapor Pressure: 1.69E-05mmHg at 25°C
• Melting Point: 88 °C(lit.)
• Refractive Index: 1.46
• Boiling Point: 339.502 °C at 760 mmHg
• PKA: 4.53±0.10(Predicted)
• Flash Point: 159.125 °C
• PSA: 75.63000
• Density: 1.102 g/cm³
• LogP: 1.62270
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 203.11575802
• Heavy Atom Count: 14
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

(S)-3-(Boc-amino)-2-methylpropionic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-3-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acid

There total 5 articles about (S)-3-((tert-Butoxycarbonyl)amino)-2-methylpropanoic 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: 96.0%

(S)-tert-butyl (2-methyl-3-oxopropyl)carbamate (374729-55-2) → (2S)-3-[(tert-butoxycarbonyl)amino]-2-methylpropanoic acid (190897-47-3)

Guidance literature:

With sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; for 5h; optical yield given as %ee;

DOI:10.1002/anie.201000955

Reference yield: 93.0%

C19H26N2O5 → (2S)-3-[(tert-butoxycarbonyl)amino]-2-methylpropanoic acid (190897-47-3)

Guidance literature:

With lithium hydroxide monohydrate; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 2.5h;

DOI:10.1248/cpb.c18-00072

Reference yield: 87.0%

methyl (S)-3-(tert-butoxycarbonylamino)-2-methylpropanoate (168828-18-0) → (2S)-3-[(tert-butoxycarbonyl)amino]-2-methylpropanoic acid (190897-47-3)

Guidance literature:

methyl (S)-3-(tert-butoxycarbonylamino)-2-methylpropanoate; With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 15h;

With hydrogenchloride; In water; ethyl acetate;

upstream raw materials:

methyl (S)-3-(tert-butoxycarbonylamino)-2-methylpropanoate

(S)-tert-butyl (2-methyl-3-oxopropyl)carbamate

Downstream raw materials:

(S)-(+)-β²-homoalanine

Boc-β²hAla-β³Leu-OBn

N-(tert-butoxycarbonyl)-α-(S)-methyl-β-alanine benzyl ester

Refernces

• 1、 Zhang, Xiaowei,Cao, Bonan,Yu, Shichao,Zhang, Xumu. "Rhodium-catalyzed asymmetric hydroformylation of n-allvlamides: Highly enantioselective approach to β2-amino aldehydes". supporting information; experimental part. p. 4047 - 4050. Retrieved 2010/08/07.
• 2、 -. "ANTITHROMBOTIC ETHERS". Page 169. . Retrieved 2008/06/13.