N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide

Base Information

• Chemical Name: N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide
• CAS No.: 167867-38-1
• Molecular Formula: C₃₂H₅₁N₅O₇S
• Molecular Weight: 649.852

Synonyms:N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide

Chemical Property of N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide

Chemical Property:

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Technology Process of N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide

There total 9 articles about N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide 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: 84.0%

N-tert-butyloxycarbonylasparagine (7536-55-2) + (3S,4aS,8aS)-2-((S)-2-Amino-3-phenyl-propane-1-sulfonyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (167867-55-2) → N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide (167867-38-1)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; 1.) 0 deg C, 1 h, 2.) r.t., overnight;

DOI:10.1021/jo00121a038

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide (167867-38-1)

Guidance literature:

Multi-step reaction with 9 steps

1: Et₃N

2: NaBH₄ / methanol

3: 96 percent / Et₃N

4: 93 percent / Cs₂CO₃ / dimethylformamide / Ambient temperature

5: Ac₂O, Cl₂ / CH₂Cl₂ / 1 h / -18 - -10 °C

6: 76 percent / N-methylmorpholine / CH₂Cl₂ / Ambient temperature

7: 98 percent / NaIO₄, aq. RuCl₃

8: 91 percent / TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

9: 84 percent / HOBt, DCC / tetrahydrofuran; dimethylformamide / 1.) 0 deg C, 1 h, 2.) r.t., overnight

With 4-methyl-morpholine; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; acetic anhydride; chlorine; benzotriazol-1-ol; caesium carbonate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a038

Reference yield:

(C5H9O2)C9H9NO(O)(CO2C2H5) (119153-87-6) → N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide (167867-38-1)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBH₄ / methanol

2: 96 percent / Et₃N

3: 93 percent / Cs₂CO₃ / dimethylformamide / Ambient temperature

4: Ac₂O, Cl₂ / CH₂Cl₂ / 1 h / -18 - -10 °C

5: 76 percent / N-methylmorpholine / CH₂Cl₂ / Ambient temperature

6: 98 percent / NaIO₄, aq. RuCl₃

7: 91 percent / TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

8: 84 percent / HOBt, DCC / tetrahydrofuran; dimethylformamide / 1.) 0 deg C, 1 h, 2.) r.t., overnight

With 4-methyl-morpholine; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; acetic anhydride; chlorine; benzotriazol-1-ol; caesium carbonate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a038

upstream raw materials:

N-tert-butyloxycarbonylasparagine

(3S,4aS,8aS)-2-((S)-2-Amino-3-phenyl-propane-1-sulfonyl)-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

N-tert-butoxycarbonyl-L-phenylalanine

(C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅)

Downstream raw materials:

(S)-2-Amino-N¹-[(S)-1-benzyl-2-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinoline-2-sulfonyl)-ethyl]-succinamide

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