Ureidovaline

Base Information

• Chemical Name: Ureidovaline
• CAS No.: 154212-61-0
• Molecular Formula: C14H23N3O3S
• Molecular Weight: 313.421
• Hs Code.: 2934100090
• European Community (EC) Number: 680-588-9
• UNII: 10433TZP2U
• DSSTox Substance ID: DTXSID30165570
• Nikkaji Number: J1.631.657A
• Wikidata: Q27251101
• Mol file: 154212-61-0.mol

Synonyms:154212-61-0;Ureidovaline;N-[2-Isopropylthiazol-4-ylmethyl(methyl)carbamoyl]-L-valine;(S)-2-(3-((2-isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid;Ritonavir impurity A [EP];UNII-10433TZP2U;(((2-isopropylthiazol-4-yl)methyl)(methyl)carbamoyl)-L-valine;10433TZP2U;N-[[N-Methyl-N-[(2-isopropyl]-4-thiazolyl)methyl)amino]carbonyl-L-valine Carboxylic Acid;Ritonavir impurity, ureidovaline- [USP];L-Valine, N-((methyl((2-(1-methylethyl)-4-thiazolyl)methyl)amino)carbonyl)-;(2S)-3-Methyl-2-((methyl((2-(1-methylethyl)thiazol-4-yl)methyl)carbamoyl)amino)butanoic acid;(2S)-3-Methyl-2-[[methyl[[2-(1-methylethyl)thiazol-4-yl]methyl]carbamoyl]amino]butanoic Acid;N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine;(2S)-3-methyl-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]butanoic Acid;SCHEMBL1389204;N-[[N-Methyl-N-[(2-isopropyl-4-thiazolyl)methyl]amino]carbonyl]-L-valine;DTXSID30165570;OSQWRZICKAOBFA-NSHDSACASA-N;BCP11230;MFCD07369527;AKOS015896181;AC-4344;CS-O-10636;DS-1850;(2s)-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanoic acid;RITONAVIR IMPURITY A [EP IMPURITY];A809509;J-502162;Q27251101;RITONAVIR IMPURITY, UREIDOVALINE- [USP IMPURITY];N-[2-Isopropylthiazol-4-ylmethyl-(methyl)carbamoyl]-L-valine;N-[N-(2-Isopropyl-4-thiazolylmethyl)-N-methylcarbamoyl]-L-valine;N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)-carbonyl)-L-valine;N-[[[(2-Isopropyl-4-thiazolyl)methyl](methyl)amino]carbonyl]-L-valine;N-[[Methyl[[2-(1-methylethyl)-4-thiazolyl]methyl]amino]carbonyl]-L-valine;(R)-2-(3-((2-isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid;2-[[(2-isopropylthiazol-4-yl)methyl-methyl-carbamoyl]amino]-3-methyl-butanoic acid;L-Valine, N-[[methyl[[2-(1-methylethyl)-4-thiazolyl]methyl]amino]carbonyl]-;(2S)-3-Methyl-2-[[methyl[[2-(1-methylethyl)thiazol-4-yl]methyl]carbamoyl]-amino]butanoic Acid;Ritonavir Imp. A (EP);Ritonavir Impurity A

Chemical Property of Ureidovaline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.545
• Boiling Point: 532.573 °C at 760 mmHg
• PKA: 4.39±0.10(Predicted)
• Flash Point: 275.89 °C
• PSA: 110.77000
• Density: 1.193 g/cm³
• LogP: 2.90800
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 313.14601278
• Heavy Atom Count: 21
• Complexity: 377

Purity/Quality:

99.9% ^*data from raw suppliers

N-[[N-Methyl-N-[(2-isopropyl]-4-thiazolyl)methyl)amino]carbonyl-L-valineCarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=NC(=CS1)CN(C)C(=O)NC(C(C)C)C(=O)O
• Isomeric SMILES: CC(C)C1=NC(=CS1)CN(C)C(=O)N[C@@H](C(C)C)C(=O)O
• Uses: N-[[N-Methyl-N-[(2-isopropyl]-4-thiazolyl)methyl)amino]carbonyl-L-valine Carboxylic Acid (Ritonavir EP Impurity A) is an intermediate in the synthesis of Ritonavir. An intermediate in the synthesis of Ritonavir.

Technology Process of Ureidovaline

There total 14 articles about Ureidovaline 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: 93.0%

N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester (154248-99-4) → N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)-carbonyl)-L-valine (154212-61-0)

Guidance literature:

N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester; With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 1.5h;

With hydrogenchloride; water; In tetrahydrofuran;

Reference yield: 83.0%

(2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid (126147-70-4) + N-methyl-N-<(2-isopropyl-4-thiazolyl)methyl>amine (154212-60-9) → N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)-carbonyl)-L-valine (154212-61-0)

Guidance literature:

With NaH; In tetrahydrofuran; water; toluene;

Reference yield: 82.0%

LiOH monohydrate + (2S)-3-Methyl-2-(phenoxycarbonyl)aminobutyric acid (126147-70-4) + N-methyl-N-<(2-isopropyl-4-thiazolyl)methyl>amine (154212-60-9) + phenol (108-95-2,27073-41-2) → N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)-carbonyl)-L-valine (154212-61-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; toluene;

upstream raw materials:

N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester

L-valine methylester hydrochloride

N-methyl-N-<(2-isopropyl-4-thiazolyl)methyl>amine

N-<<(4-nitrophenyl)oxy>carbonyl>-L-valine methyl ester

Downstream raw materials:

C₃₂H₄₅N₅O₂S

C₄₆H₆₆N₈O₄S₂

(2S)-N-((1S)-1-benzyl-2-((4S,5S)-4-benzyl-2-oxo-1,3-oxazolidin-5-yl)ethyl)-2-(((((2-isopropyl-1,3-thiazol-4-yl)methyl)amino)carbonyl)amino)-3-methylbutanamide

(2S,3S,5S)-2-[N-[N-[[N-methyl-N-[(2-isopropyl-4-thiazolyl)methyl]amino]carbonyl]valinyl]amino]-5-(t-butyloxycarbonylamino)-1,6-diphenyl-3-hydroxyhexane

Refernces

• 1、 Liu, Hongtao,Xu, Lianhong,Hui, Hon,Vivian, Randy,Callebaut, Christian,Murray, Bernard P.,Hong, Allen,Lee, Melody S.,Tsai, Luong K.,Chau, Jennifer K.,Stray, Kirsten M.,Cannizzaro, Carina,Choi, You-Chul,Rhodes, Gerry R.,Desai, Manoj C.. "Structure-activity relationships of diamine inhibitors of cytochrome P450 (CYP) 3A as novel pharmacoenhancers, part I: Core region". . p. 989 - 994. Retrieved 2014/02/14.
• 2、 -. "HIV protease inhibiting compounds". Page/Page column 104. . Retrieved 2011/01/12.