{(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester
• CAS No.: 573968-50-0
• Molecular Formula: C₃₇H₅₃N₅O₈
• Molecular Weight: 695.857

Synonyms:{(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester

Chemical Property of {(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of {(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester

There total 3 articles about {(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester 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: 58.0%

t-Boc-L-valine (13734-41-3) + (2R,3S)-3-Amino-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-yl)-4-phenyl-butyramide; hydrochloride → {(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester (573968-50-0)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1016/S0968-0896(03)00054-3

Reference yield:

(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester (116565-10-7) → {(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester (573968-50-0)

Guidance literature:

Multi-step reaction with 4 steps

1: LiOH / methanol; tetrahydrofuran; H₂O

2: 64 percent / HBTU; DIPEA / tetrahydrofuran / 2 h / 20 °C

3: HCl / dioxane / 20 °C

4: 58 percent / HBTU; DIPEA / dimethylformamide / 18 h / 20 °C

With hydrogenchloride; lithium hydroxide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00054-3

Reference yield:

[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (336611-71-3) → {(S)-1-[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-trien-11-ylcarbamoyl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid tert-butyl ester (573968-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / dioxane / 20 °C

2: 58 percent / HBTU; DIPEA / dimethylformamide / 18 h / 20 °C

With hydrogenchloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00054-3

upstream raw materials:

t-Boc-L-valine

(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

[(1S,2R)-1-Benzyl-2-hydroxy-2-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

Downstream raw materials:

(2R,3S)-3-{(S)-2-[(S)-2-Acetylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-methyl-butyrylamino}-2-hydroxy-N-((8S,11S)-8-isopropyl-7,10-dioxo-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1⁽¹⁶⁾,13⁽¹⁷⁾,14-trien-11-yl)-4-phenyl-butyramide

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