(2S)-benzyl 6-formamido-2-[(4S)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoate

Base Information

• Chemical Name: (2S)-benzyl 6-formamido-2-[(4S)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoate
• CAS No.: 1378235-11-0
• Molecular Formula: C₂₄H₂₇N₃O₆
• Molecular Weight: 453.495

Synonyms:(2S)-benzyl 6-formamido-2-[(4S)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoate

Chemical Property of (2S)-benzyl 6-formamido-2-[(4S)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoate

Chemical Property:

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Technology Process of (2S)-benzyl 6-formamido-2-[(4S)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoate

There total 7 articles about (2S)-benzyl 6-formamido-2-[(4S)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoate 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: 24.0%

(2S)-benzyl 2-amino-6-formamidohexanoate (1378235-09-6) + (4S)-2-[2-hydroxyphenyl]-Δ2-1,3-oxazoline-4-carboxylic acid (155880-02-7) → (2S)-benzyl 6-formamido-2-[(4S)-2-(2-hydroxyphenyl)-Δ2-1,3-oxazoline-4-carboxamido]hexanoate (1378235-11-0)

Guidance literature:

With triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; at 25 ℃; Inert atmosphere;

DOI:10.1021/np200972s

Reference yield:

(S)-benzyl 2-(2-(benzyloxy)benzamido)-3-hydroxypropanoate (188743-65-9) → (2S)-benzyl 6-formamido-2-[(4S)-2-(2-hydroxyphenyl)-Δ2-1,3-oxazoline-4-carboxamido]hexanoate (1378235-11-0)

Guidance literature:

Multi-step reaction with 3 steps

1: hexaammonium heptamolybdate tetrahydrate / toluene / 110 °C / Dean-Stark; Inert atmosphere

2: 10% Pd/C; hydrogen / methanol / 1 h / 25 °C / 2280.15 Torr

3: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / Inert atmosphere

With hexaammonium heptamolybdate tetrahydrate; 10% Pd/C; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; toluene;

DOI:10.1021/np200972s

Reference yield:

(4S)-benzyl 2-[2-(benzyloxy)phenyl]-Δ2-1,3-oxazoline-4-carboxylate (188743-67-1) → (2S)-benzyl 6-formamido-2-[(4S)-2-(2-hydroxyphenyl)-Δ2-1,3-oxazoline-4-carboxamido]hexanoate (1378235-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 10% Pd/C; hydrogen / methanol / 1 h / 25 °C / 2280.15 Torr

2: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / Inert atmosphere

With 10% Pd/C; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol;

DOI:10.1021/np200972s

upstream raw materials:

Fmoc-Lys-OH

(S)-benzyl 2-(2-(benzyloxy)benzamido)-3-hydroxypropanoate

(4S)-benzyl 2-[2-(benzyloxy)phenyl]-Δ²-1,3-oxazoline-4-carboxylate

(2S)-({[(9H-fluoren-9-yl)methyloxy]carbonyl}amino)-6-formamidohexanoic acid

Downstream raw materials:

(2S)-6-formamido-2-[(4S)-2-(2-hydroxyphenyl)-Δ²-1,3-oxazoline-4-carboxamido]hexanoic acid

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