(4R,5S,4'R,5'S,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'R,5'S,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.:293734-26-6
Molecular Formula:C₄₁H₄₂N₄O₅
Molecular Weight:670.808
Hs Code.:

(4R,5S,4'R,5'S,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

Synonyms:(4R,5S,4'R,5'S,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

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Chemical Property of (4R,5S,4'R,5'S,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

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Technology Process of (4R,5S,4'R,5'S,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 8 articles about (4R,5S,4'R,5'S,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: 96.0%

: 293734-25-5
(4S,5R,2'R,3'S,2''S)-3-{[2'-aziridinyl-1'-(2''-fluorenylmethoxycarbonylamino-4''-methylpentanoyl)-3'-phenyl]carbonyl}-1,5-dimethyl-4-phenylimidazolin-2-one

: 293734-26-6
(4R,5S,4'R,5'S,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

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1002/1099-0690(200007)2000:13<2489::aid-ejoc2489>3.3.co;2-z

Reference yield: 80.0%

: 103321-59-1
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine, acid chloride

: 293734-24-4
3-[(2'-aziridinyl-3'-phenyl)carbonyl]-(4S,5R,2'R,3'S)-1,5-dimethyl-4-phenyl-imidazolin-2-one

: 293734-25-5
(4S,5R,2'R,3'S,2''S)-3-{[2'-aziridinyl-1'-(2''-fluorenylmethoxycarbonylamino-4''-methylpentanoyl)-3'-phenyl]carbonyl}-1,5-dimethyl-4-phenylimidazolin-2-one

: 293734-26-6
(4R,5S,4'R,5'S,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

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:

: 102-92-1,17082-09-6
Cinnamoyl chloride

: 293734-26-6
(4R,5S,4'R,5'S,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

Guidance literature:: Multi-step reaction with 5 steps

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

2: 18 percent / MgBr₂*OEt₂ / CH₂Cl₂ / 72 h / 20 °C

3: 70 percent / AlMe₂Cl; TEA / CH₂Cl₂; hexane / 3 h

4: 80 percent / TEA; DMAP / CH₂Cl₂ / 4 h

5: 96 percent / BF₃*Et₂O / CH₂Cl₂ / 6 h / 20 °C

With dmap; TEA; boron trifluoride diethyl etherate; dimethylaluminum chloride; N-ethyl-N,N-diisopropylamine; copper(l) chloride; magnesium bromide; In hexane; dichloromethane; 1: Condensation / 2: Addition / 3: Cyclization / 4: Condensation / 5: Ring expansion;
DOI:10.1002/1099-0690(200007)2000:13<2489::aid-ejoc2489>3.3.co;2-z