L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1R)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-(9CI)

Base Information

• Chemical Name: L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1R)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-(9CI)
• CAS No.: 211918-97-7
• Molecular Formula: C₂₂H₃₀FN₃O₇
• Molecular Weight: 467.495
• DSSTox Substance ID: DTXSID00420587
• Nikkaji Number: J2.523.917B
• Wikidata: Q82231883
• Mol file: 211918-97-7.mol

Synonyms:211918-97-7;L-alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1R)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-;L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1R)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]- (9CI);DTXSID00420587;(3R)-3-[(Z-Val-Ala-)Amino]-4-oxo-5-fluoropentanoic acid methyl ester;N-[(Benzyloxy)carbonyl]-L-valyl-N-[(3R)-5-fluoro-1-methoxy-1,4-dioxopentan-3-yl]-L-alaninamide

Chemical Property of L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1R)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-(9CI)

Chemical Property:

• Vapor Pressure: 2.62E-21mmHg at 25°C
• Boiling Point: 732.4°C at 760 mmHg
• Flash Point: 396.7°C
• Density: 1.214g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 14
• Exact Mass: 467.20677847
• Heavy Atom Count: 33
• Complexity: 696

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C(C(=O)NC(C)C(=O)NC(CC(=O)OC)C(=O)CF)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: C[C@@H](C(=O)N[C@H](CC(=O)OC)C(=O)CF)NC(=O)[C@H](C(C)C)NC(=O)OCC1=CC=CC=C1

Technology Process of L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1R)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-(9CI)

There total 7 articles about L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1R)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-(9CI) 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:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + 4-[(S)-11-(9H-fluoren-9-yl)-6-(fluoromethyl)-7-(2-methoxy-2-oxoethyl)-3,9-dioxo-10-oxa-2,4,5,8-tetraazaundec-5-en-1-yl]cyclohexane-1-carboxylic acid → (S)-3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-5-fluoro-4-oxo-pentanoic acid methyl ester (634911-81-2,187389-52-2,211918-97-7)

Guidance literature:

4-[(S)-11-(9H-fluoren-9-yl)-6-(fluoromethyl)-7-(2-methoxy-2-oxoethyl)-3,9-dioxo-10-oxa-2,4,5,8-tetraazaundec-5-en-1-yl]cyclohexane-1-carboxylic acid; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

With piperidine; In N,N-dimethyl-formamide; for 0.166667h;

(S)-N-(benzyloxycarbonyl)valine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Further stages;

DOI:10.1039/d1ra03046a

Reference yield:

tert-butyl (S)-3-{[(9H-fluoren-9-yl)methoxycarbonyl]amino}-5-bromo-4-oxopentanoate (294860-44-9) → (S)-3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-5-fluoro-4-oxo-pentanoic acid methyl ester (634911-81-2,187389-52-2,211918-97-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Reflux

2.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

3.1: chloro-trimethyl-silane / 20 °C

4.1: sodium acetate / water; ethanol / 3 h / Inert atmosphere; Reflux

5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C

5.2: 0.17 h

With chloro-trimethyl-silane; tetrabutyl ammonium fluoride; sodium acetate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/d1ra03046a

Reference yield:

methyl (S)-3-{[(9H-fluoren-9-yl)methoxycarbonyl]amino}-5-bromo-4-oxopentanoate → (S)-3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-5-fluoro-4-oxo-pentanoic acid methyl ester (634911-81-2,187389-52-2,211918-97-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Reflux

2.1: sodium acetate / water; ethanol / 3 h / Inert atmosphere; Reflux

3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C

3.2: 0.17 h

With tetrabutyl ammonium fluoride; sodium acetate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1039/d1ra03046a

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

tert-butyl (S)-3-{[(9H-fluoren-9-yl)methoxycarbonyl]amino}-5-bromo-4-oxopentanoate