(R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylpentanoic acid

Base Information

Chemical Name:(R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylpentanoic acid
CAS No.:1563183-15-2
Molecular Formula:C₂₅H₂₇Cl₂FN₂O₄
Molecular Weight:509.405
Hs Code.:

Synonyms:(R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylpentanoic acid

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Chemical Property of (R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylpentanoic acid

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Technology Process of (R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylpentanoic acid

There total 2 articles about (R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylpentanoic acid 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:

: 60144-53-8
N-(tert-butoxycarbonyl)-4-fluoroaniline

: 1563183-15-2
(R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylpentanoic acid

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: caesium carbonate / N,N-dimethyl-formamide / 0.5 h

4.2: 4 h / 20 °C

5.1: lithium hydroxide; water / tetrahydrofuran / 12 h / Reflux; Inert atmosphere

With water; tert.-butyl lithium; caesium carbonate; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ml400528y

Reference yield:

: 345938-08-1
4’-(tert-butoxycarbonyl)-6-fluoro-spiro[4H-3,1-benzoxazine-4,4’-piperidin]-2(1H)-one

: 1563183-15-2
(R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylpentanoic acid

Guidance literature:: Multi-step reaction with 4 steps

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

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

3.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h

3.2: 4 h / 20 °C

4.1: lithium hydroxide; water / tetrahydrofuran / 12 h / Reflux; Inert atmosphere

With water; caesium carbonate; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ml400528y

Reference yield: 85.0%

: 1563183-15-2
(R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methylpentanoic acid

: 160067-48-1
2-amino-N-(2-hydroxyethyl)-3-phenylpropanamide

: 1563181-94-1
(R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-((R)-1-(2-hydroxyethylamino)-1-oxo-3-phenylpropan-2-yl)-2-methylpentanamide

Guidance literature:: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ml400528y