(S)-2-Amino-N¹-[(R)-2-{(S)-2-[(S)-1-(carbamoylmethyl-carbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(2,4,6-trimethyl-benzylsulfanylmethyl)-ethyl]-succinamide; hydrochloride

Base Information

• Chemical Name: (S)-2-Amino-N¹-[(R)-2-{(S)-2-[(S)-1-(carbamoylmethyl-carbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(2,4,6-trimethyl-benzylsulfanylmethyl)-ethyl]-succinamide; hydrochloride
• CAS No.: 78221-64-4
• Molecular Formula: C₃₀H₄₇N₇O₆S*ClH
• Molecular Weight: 670.273

Synonyms:

Chemical Property of (S)-2-Amino-N¹-[(R)-2-{(S)-2-[(S)-1-(carbamoylmethyl-carbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(2,4,6-trimethyl-benzylsulfanylmethyl)-ethyl]-succinamide; hydrochloride

Chemical Property:

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Technology Process of (S)-2-Amino-N¹-[(R)-2-{(S)-2-[(S)-1-(carbamoylmethyl-carbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(2,4,6-trimethyl-benzylsulfanylmethyl)-ethyl]-succinamide; hydrochloride

There total 7 articles about (S)-2-Amino-N¹-[(R)-2-{(S)-2-[(S)-1-(carbamoylmethyl-carbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(2,4,6-trimethyl-benzylsulfanylmethyl)-ethyl]-succinamide; hydrochloride 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:

o-nitrobenzenesulfenyl-L-asparaginyl-S-(2,4,6-trimethylbenzyl)-L-cysteinyl-L-prolyl-glycine amide (78221-63-3) → (S)-2-Amino-N1-[(R)-2-{(S)-2-[(S)-1-(carbamoylmethyl-carbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(2,4,6-trimethyl-benzylsulfanylmethyl)-ethyl]-succinamide; hydrochloride (78221-64-4)

Guidance literature:

With hydrogenchloride; In diethyl ether; N,N-dimethyl-formamide; for 0.0833333h; Ambient temperature;

DOI:10.1135/cccc19810286

Reference yield:

melanostatin (2002-44-0) → (S)-2-Amino-N1-[(R)-2-{(S)-2-[(S)-1-(carbamoylmethyl-carbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(2,4,6-trimethyl-benzylsulfanylmethyl)-ethyl]-succinamide; hydrochloride (78221-64-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / dicyclohexylcarbodiimide, hydroxybenzotriazole / dimethylformamide / 1) 0 deg C, 1 h; 2) room temp., 20 h

2: HBr / acetic acid / 0.5 h / Ambient temperature

3: 2.56 g / N-ethylpiperidine / dimethylformamide / 48 h / Ambient temperature

4: HCl / dimethylformamide; diethyl ether / 0.08 h / Ambient temperature

With 1-ethyl-piperidine; hydrogenchloride; hydrogen bromide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In diethyl ether; acetic acid; N,N-dimethyl-formamide;

DOI:10.1135/cccc19810286

Reference yield:

S-(2,4,6-trimethylbenzyl)-L-cysteine (78221-55-3) → (S)-2-Amino-N1-[(R)-2-{(S)-2-[(S)-1-(carbamoylmethyl-carbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(2,4,6-trimethyl-benzylsulfanylmethyl)-ethyl]-succinamide; hydrochloride (78221-64-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 69 percent / NaOH / H₂O / 0.5 h / Ambient temperature

2: 86 percent / dicyclohexylcarbodiimide, hydroxybenzotriazole / dimethylformamide / 1) 0 deg C, 1 h; 2) room temp., 20 h

3: HBr / acetic acid / 0.5 h / Ambient temperature

4: 2.56 g / N-ethylpiperidine / dimethylformamide / 48 h / Ambient temperature

5: HCl / dimethylformamide; diethyl ether / 0.08 h / Ambient temperature

With 1-ethyl-piperidine; hydrogenchloride; sodium hydroxide; hydrogen bromide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In diethyl ether; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1135/cccc19810286

upstream raw materials:

o-nitrobenzenesulfenyl-L-asparaginyl-S-(2,4,6-trimethylbenzyl)-L-cysteinyl-L-prolyl-glycine amide

melanostatin

S-(2,4,6-trimethylbenzyl)-L-cysteine

2-chloromethyl-1,3,5-trimethylbenzene

Downstream raw materials:

o-nitrobenzenesulfenyl-L-glutaminyl-L-asparaginyl-S-(2,4,6-trimethylbenzyl)-L-cysteinyl-L-prolyl-L-leucyl-glycine amide

C₄₂H₆₂N₁₂O₁₀S₂*ClH

o-nitrobenzenesulfenyl-L-glutaminyl-L-asparaginyl-S-(2,4,6-trimethylbenzyl)-L-cysteinyl-L-prolyl-N^G-p-toluenesulfonyl-L-arginyl-glycine amide

C₄₁H₆₆N₁₀O₉S*ClH

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