2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

Base Information

Chemical Name:2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester
CAS No.:1563183-08-3
Molecular Formula:C₄₃H₄₆Cl₂FN₅O₆
Molecular Weight:818.773
Hs Code.:

2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

Synonyms:2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

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Chemical Property of 2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

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Technology Process of 2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

There total 13 articles about 2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl 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: 98.0%

: 1519046-57-1
(S)-benzyl 2-(2-amino-3-phenylpropanamido)ethylcarbamate

: 1563183-04-9
(S)-2-(trimethylsilyl)ethyl 2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoate

: 1563183-08-3
2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

Guidance literature:: (S)-2-(trimethylsilyl)ethyl 2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylbutanoate; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

(S)-benzyl 2-(2-amino-3-phenylpropanamido)ethylcarbamate; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;
DOI:10.1021/ml400528y

Reference yield:

: 79099-07-3
N-tert-butyloxycarbonylpiperidin-4-one

: 1563183-08-3
2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 4.5 h / -78 - -15 °C / Inert atmosphere

1.2: 0.42 h / -78 °C / Inert atmosphere

1.3: 13 h / -78 - 70 °C / Inert atmosphere

2.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere; Molecular sieve

3.1: trifluoroacetic acid / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

4.1: 1,2-dichloro-ethane / 3 h / 20 °C / Molecular sieve; Inert atmosphere

4.2: 18 h / 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.2: 18 h / 20 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; tert.-butyl lithium; caesium carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ml400528y

Reference yield:

: 5807-30-7
3,4-dichlorophenyl acetic acid

: 1563183-08-3
2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; pentane / 2 h / -25 °C / Inert atmosphere

1.2: 1.27 h / -25 - 20 °C / Inert atmosphere

2.1: thionyl chloride / 11.33 h / 20 °C / Inert atmosphere; Cooling with ice

3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 5 h / 0 - 20 °C / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

4.1: lithium hydroxide; water / methanol / 10 h / Reflux

5.1: ethyl acetate / Resolution of racemate; Inert atmosphere

6.1: hydrogenchloride / ethyl acetate; water

7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; pyridine / tetrahydrofuran / 18 h / 40 °C / Inert atmosphere

8.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 6 h / 20 °C / Darkness

8.2: 12 h / 20 °C

9.1: 1,2-dichloro-ethane / 3 h / 20 °C / Molecular sieve; Inert atmosphere

9.2: 18 h / 20 °C / Inert atmosphere

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

10.2: 18 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; osmium(VIII) oxide; thionyl chloride; tetrabutyl ammonium fluoride; water; sodium hydride; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil; pentane;
DOI:10.1021/ml400528y