N-(N-cyclohexyl-N-ethyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Base Information

• Chemical Name: N-(N-cyclohexyl-N-ethyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine
• CAS No.: 190846-63-0
• Molecular Formula: C₃₉H₆₉N₅O₈
• Molecular Weight: 736.006

Synonyms:N-(N-cyclohexyl-N-ethyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Chemical Property of N-(N-cyclohexyl-N-ethyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(N-cyclohexyl-N-ethyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

There total 13 articles about N-(N-cyclohexyl-N-ethyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine 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: 56.0%

acetaldehyde (75-07-0,9002-91-9) + N-(N-cyclohexyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine (190846-42-5) → N-(N-cyclohexyl-N-ethyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine (190846-63-0)

Guidance literature:

acetaldehyde; N-(N-cyclohexyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine; In tetrahydrofuran; at 23 ℃; for 0.5h;

With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 23 ℃; for 18h; Further stages.;

DOI:10.1021/jm011133d

Reference yield:

2(RS)-(2-hydroxyethyl)piperidine (1484-84-0) → N-(N-cyclohexyl-N-ethyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine (190846-63-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 43 percent / Et₃N / CH₂Cl₂ / 18 h / 23 °C

2.1: 84 percent / Et₃N / CH₂Cl₂ / 0.42 h / 17 °C

3.1: NaH / dimethylformamide / 2 h

3.2: 59 percent / dimethylformamide / 18 h

4.1: 100 percent / HCl(gas) / CH₂Cl₂ / 1.25 h / 0 °C

5.1: 78 percent / Et₃N; HgCl₂ / CH₂Cl₂ / 20 h

6.1: 99 percent / H₂ / 10percent Pd/C / ethanol / 2.5 h / 23 °C / 3102.97 Torr

7.1: 65 percent / DIPEA; bromotris(pyrrolidino)phosphonium hexafluorophosphate / CH₂Cl₂ / 4 h / 0 - 23 °C

8.1: 84 percent / piperidine / tetrahydrofuran / 1 h

9.1: 87 percent / NaBH(OAc)3; AcOH / tetrahydrofuran / 2 h / 23 °C

10.1: tetrahydrofuran / 0.5 h / 23 °C

10.2: 56 percent / NaBH(OAc)3 / tetrahydrofuran / 18 h / 23 °C

With piperidine; hydrogenchloride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; mercury dichloride; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm011133d

Reference yield:

4-HYDROXYPIPERIDINE (5382-16-1) → N-(N-cyclohexyl-N-ethyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine (190846-63-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 86 percent / CH₂Cl₂ / 56 h / 23 °C

2.1: NaH / dimethylformamide / 2 h

2.2: 59 percent / dimethylformamide / 18 h

3.1: 100 percent / HCl(gas) / CH₂Cl₂ / 1.25 h / 0 °C

4.1: 78 percent / Et₃N; HgCl₂ / CH₂Cl₂ / 20 h

5.1: 99 percent / H₂ / 10percent Pd/C / ethanol / 2.5 h / 23 °C / 3102.97 Torr

6.1: 65 percent / DIPEA; bromotris(pyrrolidino)phosphonium hexafluorophosphate / CH₂Cl₂ / 4 h / 0 - 23 °C

7.1: 84 percent / piperidine / tetrahydrofuran / 1 h

8.1: 87 percent / NaBH(OAc)3; AcOH / tetrahydrofuran / 2 h / 23 °C

9.1: tetrahydrofuran / 0.5 h / 23 °C

9.2: 56 percent / NaBH(OAc)3 / tetrahydrofuran / 18 h / 23 °C

With piperidine; hydrogenchloride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; mercury dichloride; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm011133d

upstream raw materials:

acetaldehyde

N-(N-cyclohexyl-O-t-butyl-(S)-α-aspartyl)-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

4-HYDROXYPIPERIDINE

2(RS)-(2-hydroxyethyl)piperidine

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