(S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid

Base Information

• Chemical Name: (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid
• CAS No.: 168764-00-9
• Molecular Formula: C₂₅H₃₃NO₇
• Molecular Weight: 459.54

Synonyms:(S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid

Chemical Property of (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid

Chemical Property:

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Technology Process of (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid

There total 3 articles about (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic 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: 85.7%

di-tert-butyl dicarbonate (24424-99-5) + (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-amino-propionic acid (200065-54-9) → (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid (168764-00-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1248/cpb.45.1860

Reference yield:

2-adamantyl chloroformate (53120-53-9) → (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid (168764-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 62.5 percent / 1 N NaOH / dioxane; H₂O / 3 h

2: 85.7 percent / Et₃N / dimethylformamide / Ambient temperature

With sodium hydroxide; triethylamine; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.45.1860

Reference yield:

C9H11NO3*Cu(2+)*O4S(2-) → (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid (168764-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 62.5 percent / 1 N NaOH / dioxane; H₂O / 3 h

2: 85.7 percent / Et₃N / dimethylformamide / Ambient temperature

With sodium hydroxide; triethylamine; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.45.1860

upstream raw materials:

di-tert-butyl dicarbonate

(S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-amino-propionic acid

2-adamantyl chloroformate

Downstream raw materials:

C₆₈H₉₄N₆O₁₄

Boc-Tyr(2-Adoc)-Asp(O-2-Ada)-Glu(O-cHex)-Gly-OH

C₅₉H₇₈N₄O₁₄

((S)-6-(Adamantan-2-yloxycarbonylamino)-2-{(S)-3-[4-(adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionylamino}-hexanoylamino)-acetic acid benzyl ester

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