L-Valinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-(2S,3S)-3-amino-2-(phenylsel eno)butanoyl-L-prolyl-N,N-dimethyl-

Base Information

• Chemical Name: L-Valinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-(2S,3S)-3-amino-2-(phenylsel eno)butanoyl-L-prolyl-N,N-dimethyl-
• CAS No.: 190598-43-7
• Molecular Formula: C₃₀H₄₇N₅O₆Se
• Molecular Weight: 652.693
• Mol file: 190598-43-7.mol

Synonyms:

Chemical Property of L-Valinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-(2S,3S)-3-amino-2-(phenylsel eno)butanoyl-L-prolyl-N,N-dimethyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Valinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-(2S,3S)-3-amino-2-(phenylsel eno)butanoyl-L-prolyl-N,N-dimethyl-

There total 8 articles about L-Valinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-(2S,3S)-3-amino-2-(phenylsel eno)butanoyl-L-prolyl-N,N-dimethyl- 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:

N,N-dimethyl-L-valinamide hydrochloride (154462-98-3) + (S)-1-[(2S,3S)-3-((S)-2-tert-Butoxycarbonylamino-propionylamino)-2-phenylselanyl-butyryl]-pyrrolidine-2-carboxylic acid → ((S)-1-{(1S,2S)-3-[(S)-2-((S)-1-Dimethylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-methyl-3-oxo-2-phenylselanyl-propylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester (190598-43-7)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 ℃;

DOI:10.1016/S0040-4039(97)00612-6

Reference yield:

L-N-Boc-Ala (15761-38-3) → ((S)-1-{(1S,2S)-3-[(S)-2-((S)-1-Dimethylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-methyl-3-oxo-2-phenylselanyl-propylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester (190598-43-7)

Guidance literature:

Multi-step reaction with 3 steps

1: TBTU, DIPEA / acetonitrile / 0 °C

2: TBAF / tetrahydrofuran

3: TBTU, DIPEA / acetonitrile / 0 °C

With tetrabutyl ammonium fluoride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4039(97)00612-6

Reference yield:

Phenylselenyl bromide (34837-55-3) → ((S)-1-{(1S,2S)-3-[(S)-2-((S)-1-Dimethylcarbamoyl-2-methyl-propylcarbamoyl)-pyrrolidin-1-yl]-1-methyl-3-oxo-2-phenylselanyl-propylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester (190598-43-7)

Guidance literature:

Multi-step reaction with 7 steps

3: 40 percent / PyBOP, DIPEA / acetonitrile / -78 - 0 °C

4: 4 N HCl / dioxane

5: TBTU, DIPEA / acetonitrile / 0 °C

6: TBAF / tetrahydrofuran

7: TBTU, DIPEA / acetonitrile / 0 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; acetonitrile;

DOI:10.1016/S0040-4039(97)00612-6

upstream raw materials:

N,N-dimethyl-L-valinamide hydrochloride

L-N-Boc-Ala

Phenylselenyl bromide

(2S,3S)-3-tert-Butoxycarbonylamino-2-phenylselanyl-butyric acid

Downstream raw materials:

(S)-1-{(2S,3S)-2-Phenylselanyl-3-[(S)-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-butyryl}-pyrrolidine-2-carboxylic acid ((S)-1-dimethylcarbamoyl-2-methyl-propyl)-amide