N-{(S)-1-[(2R,3S,7S,10S,13S)-3-Benzyloxycarbonylamino-7-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-10-isobutyl-2-methyl-4,9,12,15-tetraoxo-1-oxa-5,11-diaza-cyclopentadec-13-ylcarbamoyl]-2-methyl-propyl}-succinamic acid

Base Information

• Chemical Name: N-{(S)-1-[(2R,3S,7S,10S,13S)-3-Benzyloxycarbonylamino-7-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-10-isobutyl-2-methyl-4,9,12,15-tetraoxo-1-oxa-5,11-diaza-cyclopentadec-13-ylcarbamoyl]-2-methyl-propyl}-succinamic acid
• CAS No.: 628318-81-0
• Molecular Formula: C₄₁H₆₁N₇O₁₃
• Molecular Weight: 859.974

Synonyms:N-{(S)-1-[(2R,3S,7S,10S,13S)-3-Benzyloxycarbonylamino-7-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-10-isobutyl-2-methyl-4,9,12,15-tetraoxo-1-oxa-5,11-diaza-cyclopentadec-13-ylcarbamoyl]-2-methyl-propyl}-succinamic acid

Chemical Property of N-{(S)-1-[(2R,3S,7S,10S,13S)-3-Benzyloxycarbonylamino-7-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-10-isobutyl-2-methyl-4,9,12,15-tetraoxo-1-oxa-5,11-diaza-cyclopentadec-13-ylcarbamoyl]-2-methyl-propyl}-succinamic acid

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Technology Process of N-{(S)-1-[(2R,3S,7S,10S,13S)-3-Benzyloxycarbonylamino-7-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-10-isobutyl-2-methyl-4,9,12,15-tetraoxo-1-oxa-5,11-diaza-cyclopentadec-13-ylcarbamoyl]-2-methyl-propyl}-succinamic acid

There total 15 articles about N-{(S)-1-[(2R,3S,7S,10S,13S)-3-Benzyloxycarbonylamino-7-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-10-isobutyl-2-methyl-4,9,12,15-tetraoxo-1-oxa-5,11-diaza-cyclopentadec-13-ylcarbamoyl]-2-methyl-propyl}-succinamic acid 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:

N-((3S)-1-bromo-2-oxo-5-methyl-3-hexyl)-t-butoxycarboxamide (52716-49-1) → N-{(S)-1-[(2R,3S,7S,10S,13S)-3-Benzyloxycarbonylamino-7-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-10-isobutyl-2-methyl-4,9,12,15-tetraoxo-1-oxa-5,11-diaza-cyclopentadec-13-ylcarbamoyl]-2-methyl-propyl}-succinamic acid (628318-81-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

1.2: 70 percent / tetrahydrofuran / 1.5 h

2.1: NaBH₄ / methanol; 2-methoxy-ethanol / 0.33 h

2.2: 51 percent / DMAP / CH₂Cl₂ / 24 h

3.1: 89 percent / Sn(OAc)2; (i-Pr)2NEt / dimethylformamide / 17 h / 80 °C

4.1: H₂; AcOH / PtO₂ / 5 h / 20 °C

5.1: 59 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 3 h

6.1: 96 percent / sulfur trioxide pyridine complex; triethylamine / dimethylsulfoxide / 48 h

7.1: 82 percent / AcOH / H₂O / 96 h / 25 °C

8.1: 79 percent / 4-dimethylaminopyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂; dimethylformamide / 3 h

9.1: HCl / dioxane; H₂O / 2 h

10.1: HATU; (i-Pr)2NEt / dimethylformamide / 20 h

11.1: Et₂NH / Pd(PPh₃)4 / tetrahydrofuran / 0.25 h

12.1: 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 4 h

13.1: CF₃CO₂H / CH₂Cl₂ / 2 h

14.1: 2.52 mg / 4-dimethylaminopyridine; pyridine / CH₂Cl₂ / 1.5 h

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; hydrogen; tin(II) acetate; sulfur trioxide pyridine complex; sodium hydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; platinum(IV) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 2-methoxy-ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo034837z

Reference yield:

methyl (2SR,5S)-5-[N-(tert-butoxycarbonyl)amino]-2-cyano-7-methyl-4-oxooctanoate (630046-94-5) → N-{(S)-1-[(2R,3S,7S,10S,13S)-3-Benzyloxycarbonylamino-7-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-10-isobutyl-2-methyl-4,9,12,15-tetraoxo-1-oxa-5,11-diaza-cyclopentadec-13-ylcarbamoyl]-2-methyl-propyl}-succinamic acid (628318-81-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: NaBH₄ / methanol; 2-methoxy-ethanol / 0.33 h

1.2: 51 percent / DMAP / CH₂Cl₂ / 24 h

2.1: 89 percent / Sn(OAc)2; (i-Pr)2NEt / dimethylformamide / 17 h / 80 °C

3.1: H₂; AcOH / PtO₂ / 5 h / 20 °C

4.1: 59 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 3 h

5.1: 96 percent / sulfur trioxide pyridine complex; triethylamine / dimethylsulfoxide / 48 h

6.1: 82 percent / AcOH / H₂O / 96 h / 25 °C

7.1: 79 percent / 4-dimethylaminopyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂; dimethylformamide / 3 h

8.1: HCl / dioxane; H₂O / 2 h

9.1: HATU; (i-Pr)2NEt / dimethylformamide / 20 h

10.1: Et₂NH / Pd(PPh₃)4 / tetrahydrofuran / 0.25 h

11.1: 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 4 h

12.1: CF₃CO₂H / CH₂Cl₂ / 2 h

13.1: 2.52 mg / 4-dimethylaminopyridine; pyridine / CH₂Cl₂ / 1.5 h

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; hydrogen; tin(II) acetate; sulfur trioxide pyridine complex; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; platinum(IV) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 2-methoxy-ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo034837z

Reference yield:

(2S)-amino-4-methylpentanamide hydrochloride (10466-61-2) → N-{(S)-1-[(2R,3S,7S,10S,13S)-3-Benzyloxycarbonylamino-7-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-10-isobutyl-2-methyl-4,9,12,15-tetraoxo-1-oxa-5,11-diaza-cyclopentadec-13-ylcarbamoyl]-2-methyl-propyl}-succinamic acid (628318-81-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 89 percent / Sn(OAc)2; (i-Pr)2NEt / dimethylformamide / 17 h / 80 °C

2: H₂; AcOH / PtO₂ / 5 h / 20 °C

3: 59 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 3 h

4: 96 percent / sulfur trioxide pyridine complex; triethylamine / dimethylsulfoxide / 48 h

5: 82 percent / AcOH / H₂O / 96 h / 25 °C

6: 79 percent / 4-dimethylaminopyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂; dimethylformamide / 3 h

7: HCl / dioxane; H₂O / 2 h

8: HATU; (i-Pr)2NEt / dimethylformamide / 20 h

9: Et₂NH / Pd(PPh₃)4 / tetrahydrofuran / 0.25 h

10: 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 4 h

11: CF₃CO₂H / CH₂Cl₂ / 2 h

12: 2.52 mg / 4-dimethylaminopyridine; pyridine / CH₂Cl₂ / 1.5 h

With pyridine; hydrogenchloride; dmap; hydrogen; tin(II) acetate; sulfur trioxide pyridine complex; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; platinum(IV) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo034837z

upstream raw materials:

succinic acid anhydride

t-Boc-L-valine

(2S)-amino-4-methylpentanamide hydrochloride

N-((3S)-1-bromo-2-oxo-5-methyl-3-hexyl)-t-butoxycarboxamide

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