tert-butyl-N-[(9S,11R)-16-(3-fluorobenzyl)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.1²'⁶.0⁹'¹³]hexacosa-1⁽²⁵⁾,2⁽²⁶⁾,3,5,21,23-hexaen-11-yl]carbamate

Base Information

• Chemical Name: tert-butyl-N-[(9S,11R)-16-(3-fluorobenzyl)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.1²'⁶.0⁹'¹³]hexacosa-1⁽²⁵⁾,2⁽²⁶⁾,3,5,21,23-hexaen-11-yl]carbamate
• CAS No.: 1460302-45-7
• Molecular Formula: C₃₃H₃₈FN₅O₅
• Molecular Weight: 603.694

Synonyms:tert-butyl-N-[(9S,11R)-16-(3-fluorobenzyl)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.1²'⁶.0⁹'¹³]hexacosa-1⁽²⁵⁾,2⁽²⁶⁾,3,5,21,23-hexaen-11-yl]carbamate

Chemical Property of tert-butyl-N-[(9S,11R)-16-(3-fluorobenzyl)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.1²'⁶.0⁹'¹³]hexacosa-1⁽²⁵⁾,2⁽²⁶⁾,3,5,21,23-hexaen-11-yl]carbamate

Chemical Property:

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Technology Process of tert-butyl-N-[(9S,11R)-16-(3-fluorobenzyl)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.1²'⁶.0⁹'¹³]hexacosa-1⁽²⁵⁾,2⁽²⁶⁾,3,5,21,23-hexaen-11-yl]carbamate

There total 10 articles about tert-butyl-N-[(9S,11R)-16-(3-fluorobenzyl)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.1²'⁶.0⁹'¹³]hexacosa-1⁽²⁵⁾,2⁽²⁶⁾,3,5,21,23-hexaen-11-yl]carbamate 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: 80.0%

tert-butylN-[(9S,11R)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.12'6.09'13]hexacosa-1(25),2(26),3,5,21,23-hexaen-11-yl]carbamate (1460302-36-6) + 3-Fluorobenzaldehyde (456-48-4) → tert-butyl-N-[(9S,11R)-16-(3-fluorobenzyl)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.12'6.09'13]hexacosa-1(25),2(26),3,5,21,23-hexaen-11-yl]carbamate (1460302-45-7)

Guidance literature:

tert-butylN-[(9S,11R)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.1²'⁶.0⁹'¹³]hexacosa-1⁽²⁵⁾,2⁽²⁶⁾,3,5,21,23-hexaen-11-yl]carbamate; 3-Fluorobenzaldehyde; In tetrahydrofuran; at 20 ℃; for 1h;

With NaBH(OAc)3; acetic acid; at 20 ℃; for 16h;

Reference yield:

benzyl (9S,11R)-11-[(tert-butoxycarbonyl)amino]-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.12,6.09,13]hexacosa-1(25),2(26),3,5,21,23-hexaene-16-carboxylate (1460302-35-5) → tert-butyl-N-[(9S,11R)-16-(3-fluorobenzyl)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.12'6.09'13]hexacosa-1(25),2(26),3,5,21,23-hexaen-11-yl]carbamate (1460302-45-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogen; 10 wt% Pd(OH)2 on carbon / methanol / 2 h / 20 °C / 760.05 Torr

2.1: tetrahydrofuran / 1 h / 20 °C

2.2: 16 h / 20 °C

With 10 wt% Pd(OH)2 on carbon; hydrogen; In tetrahydrofuran; methanol;

Reference yield:

C39H46N4O10 → tert-butyl-N-[(9S,11R)-16-(3-fluorobenzyl)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.12'6.09'13]hexacosa-1(25),2(26),3,5,21,23-hexaen-11-yl]carbamate (1460302-45-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid / ethyl acetate; chloroform / 2 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane; N,N-dimethyl-formamide; ethyl acetate / 2 h

3.1: hydrogen; 10 wt% Pd(OH)2 on carbon / methanol / 2 h / 20 °C / 760.05 Torr

4.1: tetrahydrofuran / 1 h / 20 °C

4.2: 16 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; 10 wt% Pd(OH)2 on carbon; hydrogen; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

benzyl (9S,11R)-11-[(tert-butoxycarbonyl)amino]-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.1^2,6.0^9,13]hexacosa-1⁽²⁵⁾,2⁽²⁶⁾,3,5,21,23-hexaene-16-carboxylate

tert-butylN-[(9S,11R)-14,20-dioxo-7-oxa-13,16,19,23-tetraazatetracyclo[19.3.1.1²'⁶.0⁹'¹³]hexacosa-1⁽²⁵⁾,2⁽²⁶⁾,3,5,21,23-hexaen-11-yl]carbamate

3-Fluorobenzaldehyde

5-(3-hydroxyphenyl)nicotinic acid

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