(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-3-methylbutanoic acid

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-3-methylbutanoic acid
• CAS No.: 102507-13-1
• Molecular Formula: C10H19 N O5
• Molecular Weight: 233.265
• Hs Code.: 29225090
• European Community (EC) Number: 676-409-9
• DSSTox Substance ID: DTXSID70454339
• Nikkaji Number: J1.410.242F
• Wikidata: Q72470197
• Mol file: 102507-13-1.mol

Synonyms:102507-13-1;(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-3-methylbutanoic acid;n-boc-(s)-2-amino-3-hydroxy-3-methylbutanoic acid;boc-(s)-2-amino-3-hydroxy-3-methylbutanoic acid;N-boc-3-hydroxy-L-valine;(S)-2-N-Boc-amino-3-hydroxy-3-methylbutyric acid;(S)-N-Boc-2-Amino-3-hydroxy-3-methylbutanoic acid;(2S)-3-hydroxy-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;(s)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-methylbutanoic acid;L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-3-hydroxy-;N-(tert-butoxycarbonyl)-3-hydroxy-L-valine;(2S)-2-(N-tert-Butoxycarbonyl)amino-3-hydroxy-3-methylbutanoic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxy-3-methylbutanoic acid;MFCD03094792;N-Boc-2-amino-3-hydroxy-3-methylbutanoic acid;boc-l-ser(3,3-dimethyl);(S)-2-Boc-amino-3-hydroxy-3-methylbutyric acid;N-Boc-3-Hydroxy-L-Val-OH;SCHEMBL873787;L-Threonine,N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-;DTXSID70454339;L-Threonine, N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-;S)-Boc-beta,beta-dimethyl-serine;SZVRVSZFEDIMFM-ZCFIWIBFSA-N;AKOS015999754;CS-W014676;DS-13369;EN300-217634;(s)-n-alpha-t-butyloxycarbonyl-3,3-dimethyl-serine;(S)-(tert-butoxycarbonylamino)-3-hydroxy-3-methylbutanoic acid;3-Hydroxy-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-valine;n-(t-butoxycarbonyl)-(s)-2-amino-3-hydroxy-3-methylbutanoic acid;N-Boc-(S)-2-amino-3-hydroxy-3-methylbutanoic acid (Boc-beta,beta-diMe-L-Ser-OH)

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 116-118℃
• Boiling Point: 391.1 ºC at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 190.3 ºC
• PSA: 95.86000
• Density: 1.175 g/cm³
• LogP: 1.12610
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 233.12632271
• Heavy Atom Count: 16
• Complexity: 279

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Boc-3-hydroxy-L-valine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: R36/37/38:
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C(=O)O)C(C)(C)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](C(=O)O)C(C)(C)O
• Uses: N-Boc-3-hydroxy-L-valine is used as a reagent in the synthesis of metabolites of PPI-2458, which is a selective, irreversible inhibitor of methionine aminopeptidase-2 (MetAP2). N-Boc-3-hydroxy-L-valine is also used in the preparation of Boceprevir (B674500); an NS3 serine protease inhibitor of hepatitis C virus for the treatment of HCV infection.

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

There total 17 articles about (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-3-methylbutanoic 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: 98.9%

C11H20(2)HNO4 → N-(tert-butoxycarbonyl)-3-hydroxy-L-valine (102507-13-1,105504-72-1)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; isopropyl alcohol; at 20 ℃; Solvent; Reagent/catalyst; Green chemistry;

Reference yield: 96.0%

tert-butyl N-[(1R)-2-hydroxy-1-(hydroxymethyl)-2-methylpropyl]carbamate (473545-40-3) → N-(tert-butoxycarbonyl)-3-hydroxy-L-valine (102507-13-1,105504-72-1)

Guidance literature:

With sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In acetonitrile; at 0 - 20 ℃; pH=6.4; aq. phosphate buffer;

DOI:10.1002/anie.201004646

Reference yield: 87.0%

di-tert-butyl dicarbonate (24424-99-5) + Sodium; (S)-2-amino-3-hydroxy-3-methyl-butyrate → N-(tert-butoxycarbonyl)-3-hydroxy-L-valine (102507-13-1,105504-72-1)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 20h; Inert atmosphere; Cooling with ice;

DOI:10.1002/anie.201400928

upstream raw materials:

3-hydroxy-DL-valine

di-tert-butyl dicarbonate

tert-butyl (4R)-4-(1-hydroxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

methylmagnesium bromide

Downstream raw materials:

(S)-tert-butyl 1-(benzyloxyamino)-3-hydroxy-3-methyl-1-oxobutan-2-ylcarbamate

2-[1-(2-tert-butoxycarbonylamino-3-hydroxy-3-methyl-butyrylamino)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-oxazole-4-carboxylic acid methyl ester

(S)-2-amino-3-hydroxy-3-methylbutanoic acid

methyl (S)-2-(2,4-dinitrophenylsulfonamido)-3-hydroxy-3-methylbutanoate

Refernces

• 1、 Meng, Zhanchao,Souillart, Laetitia,Monks, Brendan,Huwyler, Nikolas,Herrmann, Jennifer,Müller, Rolf,Fürstner, Alois. "A motif-Oriented Total Synthesis of Nannocystin Ax. Preparation and Biological Assessment of Analogues". . p. 6977 - 6994. Retrieved 2018.
• 2、 Liu, Rong,Xia, Mengwei,Zhang, Yanhui,Fu, Shaomin,Liu, Bo. "The journey of total synthesis toward nannocystin Ax". . p. 1781 - 1794. Retrieved 2019.
• 3、 -. "APPLICATION OF MONOCYCLIC BETA-LACTAM COMPOUND IN PHARMACY". . . Retrieved 2021/11/04.