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

Base Information

• Chemical Name: (S)-2-Amino-N¹-[(S)-1-benzyl-2-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinoline-2-sulfonyl)-ethyl]-succinamide
• CAS No.: 167867-57-4
• Molecular Formula: C₂₇H₄₃N₅O₅S
• Molecular Weight: 549.735

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

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

Chemical Property:

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

There total 11 articles about (S)-2-Amino-N¹-[(S)-1-benzyl-2-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinoline-2-sulfonyl)-ethyl]-succinamide 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: 92.0%

N--<2(S)-benzyl>tauryl>-N'-tert-butyl-(4aS,8aS)-decahydro-3(S)-isoquinolinecarboxamide (167867-38-1) → (S)-2-Amino-N1-[(S)-1-benzyl-2-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinoline-2-sulfonyl)-ethyl]-succinamide (167867-57-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/jo00121a038

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (S)-2-Amino-N1-[(S)-1-benzyl-2-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinoline-2-sulfonyl)-ethyl]-succinamide (167867-57-4)

Guidance literature:

Multi-step reaction with 11 steps

2: Et₃N

3: NaBH₄ / methanol

4: 96 percent / Et₃N

5: 93 percent / Cs₂CO₃ / dimethylformamide / Ambient temperature

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

7: 76 percent / N-methylmorpholine / CH₂Cl₂ / Ambient temperature

8: 98 percent / NaIO₄, aq. RuCl₃

9: 91 percent / TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

10: 84 percent / HOBt, DCC / tetrahydrofuran; dimethylformamide / 1.) 0 deg C, 1 h, 2.) r.t., overnight

11: 92 percent / TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

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:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (S)-2-Amino-N1-[(S)-1-benzyl-2-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinoline-2-sulfonyl)-ethyl]-succinamide (167867-57-4)

Guidance literature:

Multi-step reaction with 10 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

10: 92 percent / TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

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

L-phenylalanine

N-tert-butoxycarbonyl-L-phenylalanine

(C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅)

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