Carbamic acid, [(1S,2S,4R)-2-hydroxy-4-methyl-5-[[(1S)-1-methyl-2-oxo-2-[(phenylmeth yl)amino]ethyl]amino]-1-(2-methylpropyl)-5-oxopentyl]-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Carbamic acid, [(1S,2S,4R)-2-hydroxy-4-methyl-5-[[(1S)-1-methyl-2-oxo-2-[(phenylmeth yl)amino]ethyl]amino]-1-(2-methylpropyl)-5-oxopentyl]-, 1,1-dimethylethyl ester
• CAS No.: 527674-73-3
• Molecular Formula: C25H41N3O5
• Molecular Weight: 463.618
• Mol file: 527674-73-3.mol

Synonyms:

Chemical Property of Carbamic acid, [(1S,2S,4R)-2-hydroxy-4-methyl-5-[[(1S)-1-methyl-2-oxo-2-[(phenylmeth yl)amino]ethyl]amino]-1-(2-methylpropyl)-5-oxopentyl]-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbamic acid, [(1S,2S,4R)-2-hydroxy-4-methyl-5-[[(1S)-1-methyl-2-oxo-2-[(phenylmeth yl)amino]ethyl]amino]-1-(2-methylpropyl)-5-oxopentyl]-, 1,1-dimethylethyl ester

There total 5 articles about Carbamic acid, [(1S,2S,4R)-2-hydroxy-4-methyl-5-[[(1S)-1-methyl-2-oxo-2-[(phenylmeth yl)amino]ethyl]amino]-1-(2-methylpropyl)-5-oxopentyl]-, 1,1-dimethylethyl ester 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: 95.0%

tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate (849409-80-9) → tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-hydroxy-1-isobutyl-4-methyl-5-oxopentylcarbamate (527674-73-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

Reference yield:

(5S,1'S)-5-<1'--3'-methylbutyl>dihydrofuran-2(3H)-one (105018-81-3) → tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-hydroxy-1-isobutyl-4-methyl-5-oxopentylcarbamate (527674-73-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 0.5 h / -78 °C

2.1: aq. LiOH / tetrahydrofuran / 8 h / 23 °C

3.1: imidazole / dimethylformamide / 24 h

4.1: EDC; HOBt; iPr₂NEt / dimethylformamide; CH₂Cl₂ / 0 - 23 °C

5.1: nBu₄NF / tetrahydrofuran / 23 °C

With 1H-imidazole; lithium hydroxide; tetrabutyl ammonium fluoride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0101803

Reference yield:

(3R,5S,1'S)-5-[1'-[(tert-butyloxycarbonyl)amino]-3'-methylbutyl]-3-methyldihydrofuran-2(3H)-one (169057-47-0) → tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-hydroxy-1-isobutyl-4-methyl-5-oxopentylcarbamate (527674-73-3)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. LiOH / tetrahydrofuran / 8 h / 23 °C

2: imidazole / dimethylformamide / 24 h

3: EDC; HOBt; iPr₂NEt / dimethylformamide; CH₂Cl₂ / 0 - 23 °C

4: nBu₄NF / tetrahydrofuran / 23 °C

With 1H-imidazole; lithium hydroxide; tetrabutyl ammonium fluoride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0101803

upstream raw materials:

tert-butyl (1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-{[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxopentylcarbamate

(5S,1'S)-5-<1'--3'-methylbutyl>dihydrofuran-2(3H)-one

(3R,5S,1'S)-5-[1'-[(tert-butyloxycarbonyl)amino]-3'-methylbutyl]-3-methyldihydrofuran-2(3H)-one

(2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2,7-dimethyl-octanoic acid

Downstream raw materials:

N-((1S,2S,4R)-5-{[(1S)-2-(benzylamino)-1-methyl-2-oxoethyl]amino}-2-hydroxy-1-isobutyl-4-methyl-5-oxopentyl)-1-methyl-2,2,4-trioxo-1,2,3,4-tetrahydro-2,1-benzothiazine-7-carboxamide

{(S)-1-[(1S,2S,4R)-4-((S)-1-Benzylcarbamoyl-ethylcarbamoyl)-2-hydroxy-1-isobutyl-pentylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid tert-butyl ester