(R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid

Base Information

• Chemical Name: (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid
• CAS No.: 26973-43-3
• Molecular Formula: C₁₃H₁₅Cl₂NO₅
• Molecular Weight: 336.172

Synonyms:(R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid

Chemical Property of (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid

Chemical Property:

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Technology Process of (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid

There total 9 articles about (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic 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: 100.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + (R)-2-amino-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid (25698-18-4) → (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid (26973-43-3)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 20 ℃; for 1h;

DOI:10.1248/cpb.53.1277

Reference yield: 52.0%

methyl (2R)-2-(3,5-dichloro-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate (191542-15-1) → (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid (26973-43-3)

Guidance literature:

methyl (2R)-2-(3,5-dichloro-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate; With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 25 ℃; for 16h;

With hydrogenchloride; In water; pH=4;

DOI:10.1021/acs.jmedchem.1c00034

Reference yield: 48.0%

D-4-hydroxyphenylglycine (22818-40-2) → (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid (26973-43-3)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(99)01283-6

upstream raw materials:

D-4-hydroxyphenylglycine

N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

(R)-2-amino-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid

Downstream raw materials:

(S)-2-{[(R)-2-tert-Butoxycarbonylamino-2-(3,5-dichloro-4-hydroxy-phenyl)-acetyl]-methyl-amino}-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

(S)-2-{[(R)-2-tert-Butoxycarbonylamino-2-(3,5-dichloro-4-hydroxy-phenyl)-acetyl]-methyl-amino}-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester

C₄₈H₄₄Cl₄IN₅O₁₃

methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-methoxyphenyl)acetate

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