N-[N-(t-butoxycarbonylmethyl)-(R)-cyclohexylalanyl]-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Base Information

Chemical Name:N-[N-(t-butoxycarbonylmethyl)-(R)-cyclohexylalanyl]-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine
CAS No.:441771-99-9
Molecular Formula:C₃₈H₆₇N₅O₈
Molecular Weight:721.979
Hs Code.:

Synonyms:N-[N-(t-butoxycarbonylmethyl)-(R)-cyclohexylalanyl]-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

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Chemical Property of N-[N-(t-butoxycarbonylmethyl)-(R)-cyclohexylalanyl]-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

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Technology Process of N-[N-(t-butoxycarbonylmethyl)-(R)-cyclohexylalanyl]-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

There total 12 articles about N-[N-(t-butoxycarbonylmethyl)-(R)-cyclohexylalanyl]-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: 72.0%

: 5292-43-3
bromoacetic acid tert-butyl ester

: 441771-98-8
N-[(R)-cyclohexylalanyl]-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

: 441771-99-9
N-[N-(t-butoxycarbonylmethyl)-(R)-cyclohexylalanyl]-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Guidance literature:: With potassium carbonate; In acetonitrile; at 20 ℃; for 30h;
DOI:10.1021/jm011133d

Reference yield:

: 58717-02-5
3-cyclohexyl-D-alanine

: 441771-99-9
N-[N-(t-butoxycarbonylmethyl)-(R)-cyclohexylalanyl]-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / aq. NaOH; aq. NaHCO₃ / dioxane / 1 h / 0 °C

2: oxalyl chloride; DMF / CH₂Cl₂ / 1.5 h

3: DIPEA / CH₂Cl₂ / 1 h / 0 °C

4: 100 percent / HCl(gas) / CH₂Cl₂ / 1.25 h / 0 °C

5: 83 percent / Et₃N; HgCl₂ / CH₂Cl₂ / 20 h

6: 63 percent / Zn; AcOH / 4 h / 20 °C

7: 72 percent / K₂CO₃ / acetonitrile / 30 h / 20 °C

With hydrogenchloride; sodium hydroxide; oxalyl dichloride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; mercury dichloride; zinc; In 1,4-dioxane; dichloromethane; acetonitrile;
DOI:10.1021/jm011133d

Reference yield:

: 1484-84-0
2(RS)-(2-hydroxyethyl)piperidine

: 441771-99-9
N-[N-(t-butoxycarbonylmethyl)-(R)-cyclohexylalanyl]-2(RS)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Guidance literature:: Multi-step reaction with 9 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: 73 percent / 1,4-cyclohexadiene / 10percent Pd/C / ethanol / 1 h

5.1: DIPEA / CH₂Cl₂ / 1 h / 0 °C

6.1: 100 percent / HCl(gas) / CH₂Cl₂ / 1.25 h / 0 °C

7.1: 83 percent / Et₃N; HgCl₂ / CH₂Cl₂ / 20 h

8.1: 63 percent / Zn; AcOH / 4 h / 20 °C

9.1: 72 percent / K₂CO₃ / acetonitrile / 30 h / 20 °C

With hydrogenchloride; cyclohexa-1,4-diene; sodium hydride; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; zinc; 10percent Pd/C; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm011133d