(4R,5S,4'S,5'R,1''S)-4-[(1',5'-dimethyl-4'-phenylimidazolin-2'-on-3'-yl)carbonyl]-2-(1''-fluorenylmethoxycarbonylamino-3''-methyl-1''-butyl)-4,5-dihydro-5-phenyloxazole

Base Information

• Chemical Name: (4R,5S,4'S,5'R,1''S)-4-[(1',5'-dimethyl-4'-phenylimidazolin-2'-on-3'-yl)carbonyl]-2-(1''-fluorenylmethoxycarbonylamino-3''-methyl-1''-butyl)-4,5-dihydro-5-phenyloxazole
• CAS No.: 293734-30-2
• Molecular Formula: C₄₁H₄₂N₄O₅
• Molecular Weight: 670.808

Synonyms:(4R,5S,4'S,5'R,1''S)-4-[(1',5'-dimethyl-4'-phenylimidazolin-2'-on-3'-yl)carbonyl]-2-(1''-fluorenylmethoxycarbonylamino-3''-methyl-1''-butyl)-4,5-dihydro-5-phenyloxazole

Chemical Property of (4R,5S,4'S,5'R,1''S)-4-[(1',5'-dimethyl-4'-phenylimidazolin-2'-on-3'-yl)carbonyl]-2-(1''-fluorenylmethoxycarbonylamino-3''-methyl-1''-butyl)-4,5-dihydro-5-phenyloxazole

Chemical Property:

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Technology Process of (4R,5S,4'S,5'R,1''S)-4-[(1',5'-dimethyl-4'-phenylimidazolin-2'-on-3'-yl)carbonyl]-2-(1''-fluorenylmethoxycarbonylamino-3''-methyl-1''-butyl)-4,5-dihydro-5-phenyloxazole

There total 5 articles about (4R,5S,4'S,5'R,1''S)-4-[(1',5'-dimethyl-4'-phenylimidazolin-2'-on-3'-yl)carbonyl]-2-(1''-fluorenylmethoxycarbonylamino-3''-methyl-1''-butyl)-4,5-dihydro-5-phenyloxazole 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: 75.0%

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine, acid chloride (103321-59-1) + (4S,5R,2'S,3'R)-1,5-dimethyl-4-phenyl-3-[(3'-phenyl-2'-aziridinyl)carbonyl]imidazolin-2-one (293734-29-9) → (4R,5S,4'S,5'R,1''S)-4-[(1',5'-dimethyl-4'-phenylimidazolin-2'-on-3'-yl)carbonyl]-2-(1''-fluorenylmethoxycarbonylamino-3''-methyl-1''-butyl)-4,5-dihydro-5-phenyloxazole (293734-30-2)

Guidance literature:

With dmap; TEA; In dichloromethane; for 4h;

DOI:10.1002/1099-0690(200007)2000:13<2489::aid-ejoc2489>3.3.co;2-z

Reference yield:

(4R,5S)-3,4-dimethyl-5-phenyl-imidazolidin-2-one (112791-04-5) → (4R,5S,4'S,5'R,1''S)-4-[(1',5'-dimethyl-4'-phenylimidazolin-2'-on-3'-yl)carbonyl]-2-(1''-fluorenylmethoxycarbonylamino-3''-methyl-1''-butyl)-4,5-dihydro-5-phenyloxazole (293734-30-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / DIPEA; CuCl / CH₂Cl₂ / 6 h / Heating

2: 72 percent / MgBr₂*OEt₂ / CH₂Cl₂ / 72 h / 20 °C

3: 60 percent / AlMe₂Cl; TEA / CH₂Cl₂; hexane / 3 h

4: 75 percent / TEA; DMAP / CH₂Cl₂ / 4 h

With dmap; TEA; dimethylaluminum chloride; N-ethyl-N,N-diisopropylamine; copper(l) chloride; magnesium bromide; In hexane; dichloromethane; 1: Condensation / 2: Addition / 3: Cyclization / 4: Cyclization;

DOI:10.1002/1099-0690(200007)2000:13<2489::aid-ejoc2489>3.3.co;2-z

Reference yield:

Cinnamoyl chloride (102-92-1,17082-09-6) → (4R,5S,4'S,5'R,1''S)-4-[(1',5'-dimethyl-4'-phenylimidazolin-2'-on-3'-yl)carbonyl]-2-(1''-fluorenylmethoxycarbonylamino-3''-methyl-1''-butyl)-4,5-dihydro-5-phenyloxazole (293734-30-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / DIPEA; CuCl / CH₂Cl₂ / 6 h / Heating

2: 72 percent / MgBr₂*OEt₂ / CH₂Cl₂ / 72 h / 20 °C

3: 60 percent / AlMe₂Cl; TEA / CH₂Cl₂; hexane / 3 h

4: 75 percent / TEA; DMAP / CH₂Cl₂ / 4 h

With dmap; TEA; dimethylaluminum chloride; N-ethyl-N,N-diisopropylamine; copper(l) chloride; magnesium bromide; In hexane; dichloromethane; 1: Condensation / 2: Addition / 3: Cyclization / 4: Cyclization;

DOI:10.1002/1099-0690(200007)2000:13<2489::aid-ejoc2489>3.3.co;2-z

upstream raw materials:

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine, acid chloride

(4S,5R,2'S,3'R)-1,5-dimethyl-4-phenyl-3-[(3'-phenyl-2'-aziridinyl)carbonyl]imidazolin-2-one

(4R,5S)-3,4-dimethyl-5-phenyl-imidazolidin-2-one

Cinnamoyl chloride

Downstream raw materials:

(4S,5R,2'S,3'R,2''S)-3-[2'-(2''-fluorenylmethoxycarbonylamino-4''-methylpentanoyl)amino-3'-hydroxy-3'-phenylpropionyl]-1,5-dimethyl-4-phenylimidazolin-2-one

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