(3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid

Base Information

• Chemical Name: (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid
• CAS No.: 252681-04-2
• Molecular Formula: C₁₇H₁₇F₂NO₃
• Molecular Weight: 321.324

Synonyms:(3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid

Chemical Property of (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid

Chemical Property:

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Technology Process of (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid

There total 2 articles about (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic 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: 71.0%

(4S)-3,3-difluoro-1-((1R)-2-hydroxy-1-phenylethyl)-4-phenylazetidin-2-one (252681-03-1) → (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid (252681-04-2)

Guidance literature:

With hydrogenchloride; In water; for 5h; Heating;

DOI:10.1021/jo990868b

Reference yield:

2,4-diphenyl-1,3-oxazolidine (249920-08-9) → (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid (252681-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / Zn / tetrahydrofuran / 1 h / Heating

2: 71 percent / HCl / H₂O / 5 h / Heating

With hydrogenchloride; zinc; In tetrahydrofuran; water; 1: Alkylation / 2: Hydrolysis;

DOI:10.1021/jo990868b

Reference yield: 95.0%

Ethyl isocyanoacetate (2999-46-4) + benzaldehyde (100-52-7) + benzylamine (100-46-9) + (3S)-2,2-difluoro-3-((1R)-2-hydroxy-1-phenylethylamino)-3-phenylpropanoic acid (252681-04-2) → (2-{Benzyl-[(S)-2,2-difluoro-3-((R)-2-hydroxy-1-phenyl-ethylamino)-3-phenyl-propionyl]-amino}-2-phenyl-acetylamino)-acetic acid ethyl ester (667938-19-4)

Guidance literature:

In methanol; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2003.11.019

upstream raw materials:

(4S)-3,3-difluoro-1-((1R)-2-hydroxy-1-phenylethyl)-4-phenylazetidin-2-one

2,4-diphenyl-1,3-oxazolidine

Downstream raw materials:

(2-{Benzyl-[(S)-2,2-difluoro-3-((R)-2-hydroxy-1-phenyl-ethylamino)-3-phenyl-propionyl]-amino}-2-phenyl-acetylamino)-acetic acid ethyl ester

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