(7S,10S,13S)-7-hydroxymethyl-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]-nona-deca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl-carbamic acid benzylester

Base Information

• Chemical Name: (7S,10S,13S)-7-hydroxymethyl-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]-nona-deca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl-carbamic acid benzylester
• CAS No.: 1020257-59-3
• Molecular Formula: C₂₈H₃₇N₃O₆
• Molecular Weight: 511.618

Synonyms:(7S,10S,13S)-7-hydroxymethyl-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]-nona-deca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl-carbamic acid benzylester

Chemical Property of (7S,10S,13S)-7-hydroxymethyl-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]-nona-deca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl-carbamic acid benzylester

Chemical Property:

Purity/Quality:

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Technology Process of (7S,10S,13S)-7-hydroxymethyl-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]-nona-deca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl-carbamic acid benzylester

There total 9 articles about (7S,10S,13S)-7-hydroxymethyl-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]-nona-deca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-13-yl-carbamic acid benzylester 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: 90.0%

(7S,10S,13S)-13-benzyloxycarbonylamino-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo-[13.2.2]nonadeca-1(18),15(19),6-triene-7-carboxylic acid methyl ester → (7S,10S,13S)-7-hydroxymethyl-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]-nona-deca-1(18),15(19),16-trien-13-yl-carbamic acid benzylester (1020257-59-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; methanol; diethyl ether; at 20 ℃; for 19h; Inert atmosphere; Cooling with ice;

Reference yield:

(S)-2-{(S)-2-[(S)-3-(4-allyloxy-phenyl)-2-tert-butoxycarbonylamino propionylamino]-3-methylbutyrylamino}-pent-4-enoic acid methyl ester → (7S,10S,13S)-7-hydroxymethyl-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]-nona-deca-1(18),15(19),16-trien-13-yl-carbamic acid benzylester (1020257-59-3)

Guidance literature:

Multi-step reaction with 5 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,1,2-trichloroethane / 21 h / Inert atmosphere; Reflux

2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 18 h / 20 °C / 760.05 Torr

3: hydrogenchloride / water; 1,4-dioxane / 16 h / 20 °C

4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C

5: lithium aluminium tetrahydride / tetrahydrofuran; methanol; diethyl ether / 19 h / 20 °C / Inert atmosphere; Cooling with ice

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; 1,1,2-trichloroethane; water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

(S)-2-[(S)-3-(4-allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester (127154-09-0) → (7S,10S,13S)-7-hydroxymethyl-10-isobutyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]-nona-deca-1(18),15(19),16-trien-13-yl-carbamic acid benzylester (1020257-59-3)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydroxide / tetrahydrofuran; water; methanol / 18 h / 20 °C

2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,1,2-trichloroethane / 21 h / Inert atmosphere; Reflux

4: hydrogen; palladium 10% on activated carbon / ethyl acetate / 18 h / 20 °C / 760.05 Torr

5: hydrogenchloride / water; 1,4-dioxane / 16 h / 20 °C

6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C

7: lithium aluminium tetrahydride / tetrahydrofuran; methanol; diethyl ether / 19 h / 20 °C / Inert atmosphere; Cooling with ice

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; 1,1,2-trichloroethane; water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

(S)-2-[(S)-3-(4-allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid

L-valine methylester hydrochloride

(S)-2-[(S)-3-(4-allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester

N-(tert-butyloxycarbonyl)-O-allyl-(S)-tyrosine

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