Boc-D-norvaline

Base Information

• Chemical Name: Boc-D-norvaline
• CAS No.: 57521-85-4
• Molecular Formula: C10H19 N O4
• Molecular Weight: 217.265
• Hs Code.: 29041000
• European Community (EC) Number: 853-674-0
• DSSTox Substance ID: DTXSID20426405
• Wikidata: Q72510352
• Mol file: 57521-85-4.mol

Synonyms:Boc-D-norvaline;57521-85-4;Boc-D-Nva-OH;(R)-2-((tert-Butoxycarbonyl)amino)pentanoic acid;D-Norvaline, N-[(1,1-dimethylethoxy)carbonyl]-;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;SCHEMBL3450517;DTXSID20426405;INWOAUUPYIXDHN-SSDOTTSWSA-N;N-(t-butoxycarbonyl)-D-norvaline;FD3024;MFCD00155638;AKOS015836452;AKOS015893978;AM82595;CS-W014816;HY-W014100;N-TERT-BUTOXYCARBONYL-D-NORVALINE;Boc-D-Nva-OH, >=98.0% (TLC);DS-15175;(R)-2-tert-butoxycarbonylamino-pentanoic acid;EN300-43850;(R)-2-(tert-butoxycarbonylamino)pentanoic acid;(R)-2-((tert-Butoxycarbonyl)amino)pentanoicacid;A847913;Q-101722;(2R)-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid

Chemical Property of Boc-D-norvaline

Chemical Property:

• Boiling Point: 348.3 °C at 760 mmHg
• PKA: 4.02±0.20(Predicted)
• Flash Point: 164.4 °C
• PSA: 75.63000
• Density: 1.081 g/cm³
• LogP: 2.15530
• Storage Temp.: Store at RT.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 217.13140809
• Heavy Atom Count: 15
• Complexity: 232

Purity/Quality:

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

Boc-D-norvaline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCC(C(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CCC[C@H](C(=O)O)NC(=O)OC(C)(C)C
• Uses: BOC-D-NVA-OH is a chemical reagent used in the preparation of benzothiophene inhibitors of MK2. Also has been used to synthesize pyrrolidine diketopiperazines to inhibit melanoma

Technology Process of Boc-D-norvaline

There total 22 articles about Boc-D-norvaline 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: 98.6%

D-norvaline (2013-12-9,498-18-0) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-D-norvaline (57521-85-4)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; at 20 ℃; for 25h;

Reference yield: 82.0%

[(R)-1-((R)-1,2-Dihydroxy-ethyl)-butyl]-carbamic acid tert-butyl ester (154079-55-7) → N-tert-butoxycarbonyl-D-norvaline (57521-85-4)

Guidance literature:

With ruthenium trichloride; sodium periodate; sodium carbonate; In tetrachloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)61565-4

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-D-norvaline (57521-85-4)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. Na₂CO₃, NaHCO₃ / dioxane / 1.) 0 deg C, overnight, 2.) 25 deg C, 8 h

2: 26 percent / Jones reagent / acetone / 2 h / 0 °C

3: H₂ / 5percent Pd/C / methanol / 3 h

With jones reagent; hydrogen; sodium hydrogencarbonate; sodium carbonate; palladium on activated charcoal; In 1,4-dioxane; methanol; acetone;

DOI:10.1016/0040-4020(96)00630-8

upstream raw materials:

di-tert-butyl dicarbonate

(2R,3R)-3-(α-phenylbenzylamino)-1,2-hexanediol

(R)-tert-butyl (1-hydroxypentan-2-yl)carbamate

[(R)-1-((R)-1,2-Dihydroxy-ethyl)-butyl]-carbamic acid tert-butyl ester

Downstream raw materials:

C₅H₁₂N₂O

C₁₀H₂₀N₂O₃

2(R)-Amino-N-[2,3,4,5-tetrahydro-2-oxo-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-1-benzazepin-3-(R)-yl]-pentanamide, mono(trifluoroacetate)

Refernces

• 1、 -. "NOVEL COMPOUNDS". Page/Page column 70. . Retrieved 2015/12/17.
• 2、 Poch, Marta. "A short enantioselective synthesis of N-Boc-α-amino acids from epoxy alcohols". . p. 7781 - 7784. Retrieved 2007/10/02.