Pentanamide, 2-(acetylamino)-4-methyl-N-(phenylmethyl)-, (S)-

Base Information

• Chemical Name: Pentanamide, 2-(acetylamino)-4-methyl-N-(phenylmethyl)-, (S)-
• CAS No.: 87783-60-6
• Molecular Formula: C15H22N2O2
• Molecular Weight: 262.352
• Mol file: 87783-60-6.mol

Synonyms:

Chemical Property of Pentanamide, 2-(acetylamino)-4-methyl-N-(phenylmethyl)-, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pentanamide, 2-(acetylamino)-4-methyl-N-(phenylmethyl)-, (S)-

There total 5 articles about Pentanamide, 2-(acetylamino)-4-methyl-N-(phenylmethyl)-, (S)- 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-acetyldehydroleucine N-benzylamide → 2-(acetylamino)-4-methyl-N-(phenylmethyl)pentanamide (87783-60-6) + Ac-D-Leu-benzylamide (177032-52-9)

Guidance literature:

With hydrogen; di-μ-chlorobis(norbornadiene)dirhodium(I); (R_P,R_P)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane; In methanol; under 760 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00314a053

Reference yield:

2-[(Z)-Acetylimino]-4-methyl-pentanoic acid benzylamide → 2-(acetylamino)-4-methyl-N-(phenylmethyl)pentanamide (87783-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / KH, tert-butyl alcohol / tetrahydrofuran / Ambient temperature

2: H₂ / (Rh(NBD)Cl)2, (R,R)-DIPAMP / methanol / 760 Torr

With hydrogen; potassium hydride; tert-butyl alcohol; di-μ-chlorobis(norbornadiene)dirhodium(I); (R_P,R_P)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane; In tetrahydrofuran; methanol;

DOI:10.1021/ja00314a053

Reference yield:

1-benzyl-2-methyl-4-isobutylimidazole (88336-73-6) → 2-(acetylamino)-4-methyl-N-(phenylmethyl)pentanamide (87783-60-6)

Guidance literature:

Multi-step reaction with 3 steps

1: DBU, hematoporphyrin, oxygen / tetrahydrofuran / 2 h / 0 °C / Irradiation

2: 83 percent / KH, tert-butyl alcohol / tetrahydrofuran / Ambient temperature

3: H₂ / (Rh(NBD)Cl)2, (R,R)-DIPAMP / methanol / 760 Torr

With hydrogen; oxygen; potassium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; hematoporphyrin; tert-butyl alcohol; di-μ-chlorobis(norbornadiene)dirhodium(I); (R_P,R_P)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane; In tetrahydrofuran; methanol;

DOI:10.1021/ja00314a053

upstream raw materials:

(S)-4-isobutyl-2-methyloxazol-5(4H)-one

benzylamine

L-leucine

1-benzyl-2-methyl-4-isobutylimidazole

Downstream raw materials:

2-methyl-4-isobutyl-5-(N-benzyltrifluoroacetamido)oxazole

Refernces

• 1、 Lipshutz, Bruce H.,Hungate, Randall W.,NcCarthy, Keith E.. "Heterocycles as Masked Diamide/Dipeptide Equivalents. Formation and Reactions of Substituted 5-(Acylamino)oxazoles as Intermediates en route to the Cyclopeptide Alkaloids". . p. 7703 - 7713. Retrieved 2007/10/02.