{(R)-1-[(S)-2-Butyl-4-(naphthalene-1-carbonyl)-piperazin-1-ylmethyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(R)-1-[(S)-2-Butyl-4-(naphthalene-1-carbonyl)-piperazin-1-ylmethyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester
• CAS No.: 169448-30-0
• Molecular Formula: C₄₆H₅₃N₃O₃S
• Molecular Weight: 728.011

Synonyms:{(R)-1-[(S)-2-Butyl-4-(naphthalene-1-carbonyl)-piperazin-1-ylmethyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester

Chemical Property of {(R)-1-[(S)-2-Butyl-4-(naphthalene-1-carbonyl)-piperazin-1-ylmethyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester

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Technology Process of {(R)-1-[(S)-2-Butyl-4-(naphthalene-1-carbonyl)-piperazin-1-ylmethyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester

There total 9 articles about {(R)-1-[(S)-2-Butyl-4-(naphthalene-1-carbonyl)-piperazin-1-ylmethyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester 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:

Boc-Nle-OH (6404-28-0) → {(R)-1-[(S)-2-Butyl-4-(naphthalene-1-carbonyl)-piperazin-1-ylmethyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester (169448-30-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / DCC / CH₂Cl₂ / 18 h

2: 1.) aq. HCl, 2.) aq. NaHCO₃ / 1.) CHCl₃

3: LiAlH₄ / tetrahydrofuran / 15 h / Heating

4: CH₂Cl₂ / 2 h

5: 100 percent / H₂ / 10percent Pd/C / methanol / 16 h

6: EDC*HCl, HOBT / dimethylformamide / 3 h

7: TFA / CH₂Cl₂ / 0.75 h

8: NaBH(OAc)3 / 1,2-dichloro-ethane / 18 h / 0 - 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9508090

Reference yield:

(S)-1-Benzyl-3-butyl-piperazine (175357-61-6,186412-45-3,928025-42-7) → {(R)-1-[(S)-2-Butyl-4-(naphthalene-1-carbonyl)-piperazin-1-ylmethyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester (169448-30-0)

Guidance literature:

Multi-step reaction with 5 steps

1: CH₂Cl₂ / 2 h

2: 100 percent / H₂ / 10percent Pd/C / methanol / 16 h

3: EDC*HCl, HOBT / dimethylformamide / 3 h

4: TFA / CH₂Cl₂ / 0.75 h

5: NaBH(OAc)3 / 1,2-dichloro-ethane / 18 h / 0 - 20 °C

With hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9508090

Reference yield:

4-Benzyl-1-tert-butoxycarbonyl-2(S)-n-butylpiperazine (169447-75-0) → {(R)-1-[(S)-2-Butyl-4-(naphthalene-1-carbonyl)-piperazin-1-ylmethyl]-2-tritylsulfanyl-ethyl}-carbamic acid tert-butyl ester (169448-30-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / H₂ / 10percent Pd/C / methanol / 16 h

2: EDC*HCl, HOBT / dimethylformamide / 3 h

3: TFA / CH₂Cl₂ / 0.75 h

4: NaBH(OAc)3 / 1,2-dichloro-ethane / 18 h / 0 - 20 °C

With hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9508090

upstream raw materials:

N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal

((S)-3-Butyl-piperazin-1-yl)-naphthalen-1-yl-methanone

1-naphthalenecarboxylic acid

Boc-Nle-OH

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