((S)-1-{(2S,4R)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

Base Information

• Chemical Name: ((S)-1-{(2S,4R)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester
• CAS No.: 928406-61-5
• Molecular Formula: C₂₄H₃₁Cl₂N₄O₅P
• Molecular Weight: 557.414

Synonyms:((S)-1-{(2S,4R)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

Chemical Property of ((S)-1-{(2S,4R)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

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Technology Process of ((S)-1-{(2S,4R)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

There total 6 articles about ((S)-1-{(2S,4R)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-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: 16.0%

[(S)-1-((S)-1-Amino-3-hydroxy-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (928406-59-1) + N,N-di(2-chloroethyl)amidophosphoric acid dichloride (127-88-8) → ((S)-1-{(2S,4R)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ5-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester (928406-61-5) + ((S)-1-{(2R,4R)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ5-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester (928406-60-4) + benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate (5241-56-5,17324-88-8,53562-23-5,4801-80-3)

Guidance literature:

With TEA; In tetrahydrofuran; at 0 - 20 ℃; for 48h;

DOI:10.1016/j.bmcl.2006.10.017

Reference yield:

Z-Phe-Hse-NH2 (928406-56-8) → ((S)-1-{(2S,4R)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ5-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester (928406-61-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / imidazole / dimethylformamide / 20 °C

2: 67 percent / bis(trifluoroacetoxy)iodobenzene / acetonitrile; H₂O / 20 °C

3: 62 percent / TBAF / tetrahydrofuran / 20 °C

4: 12 percent / TEA / tetrahydrofuran / 48 h / 0 - 20 °C

With 1H-imidazole; TEA; tetrabutyl ammonium fluoride; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; 2: Hofmann rearrangement;

DOI:10.1016/j.bmcl.2006.10.017

Reference yield:

(S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-4-hydroxy-butyric acid (928406-55-7) → ((S)-1-{(2S,4R)-2-[Bis-(2-chloro-ethyl)-amino]-2-oxo-2λ5-[1,3,2]oxazaphosphinan-4-ylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester (928406-61-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: HOBt; EDC / tetrahydrofuran / 20 °C

1.2: aq. NH₃ / tetrahydrofuran

2.1: 85 percent / imidazole / dimethylformamide / 20 °C

3.1: 67 percent / bis(trifluoroacetoxy)iodobenzene / acetonitrile; H₂O / 20 °C

4.1: 62 percent / TBAF / tetrahydrofuran / 20 °C

5.1: 12 percent / TEA / tetrahydrofuran / 48 h / 0 - 20 °C

With 1H-imidazole; TEA; tetrabutyl ammonium fluoride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile; 3.1: Hofmann rearrangement;

DOI:10.1016/j.bmcl.2006.10.017

upstream raw materials:

[(S)-1-((S)-1-Amino-3-hydroxy-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester

N,N-di(2-chloroethyl)amidophosphoric acid dichloride

Z-Phe-Hse-NH₂

(S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-4-hydroxy-butyric acid

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