[(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

Base Information

• Chemical Name: [(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
• CAS No.: 336611-71-3
• Molecular Formula: C₃₂H₄₄N₄O₇
• Molecular Weight: 596.724

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

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Technology Process of [(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

There total 2 articles about [(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 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: 64.0%

(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid (105181-72-4) + (8S,11S)-11-Amino-8-isopropyl-2-oxa-6,9-diaza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-triene-7,10-dione; compound with trifluoro-acetic acid → [(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)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 2h;

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) → [(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)

Guidance literature:

Multi-step reaction with 2 steps

1: LiOH / methanol; tetrahydrofuran; H₂O

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

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

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) → (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

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃;

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

upstream raw materials:

(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid

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

Downstream raw materials:

{(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

(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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