tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate

Base Information

• Chemical Name: tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate
• CAS No.: 1388893-83-1
• Molecular Formula: C₂₂H₃₁N₃O₄S
• Molecular Weight: 433.572

Synonyms:tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate

Chemical Property of tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate

There total 8 articles about tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-12-yl]oxy]cyclohexyl)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: 61.0%

ethyl 2-[(3S)-12-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetate (1388893-82-0) → tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate (1388893-83-1)

Guidance literature:

ethyl 2-[(3S)-12-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-3-yl]acetate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

With water; In tetrahydrofuran; Inert atmosphere;

Reference yield:

ethyl (2-oxocyclopentyl)acetate (20826-94-2) → tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate (1388893-83-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diethylamine; sulfur / ethanol / 20 °C

2.1: 20 - 180 °C / Inert atmosphere

2.2: Cooling with ice

3.1: CHIRALPAK IC / ethanol / Resolution of racemate

4.1: trichlorophosphate / 1,4-dioxane / 4 h / 110 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

6.2: Inert atmosphere

With lithium aluminium tetrahydride; sodium hydride; sulfur; diethylamine; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; ethanol; mineral oil;

Reference yield:

ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate (1029689-54-0) → tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate (1388893-83-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 20 - 180 °C / Inert atmosphere

1.2: Cooling with ice

2.1: CHIRALPAK IC / ethanol / Resolution of racemate

3.1: trichlorophosphate / 1,4-dioxane / 4 h / 110 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

5.2: Inert atmosphere

With lithium aluminium tetrahydride; sodium hydride; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; ethanol; mineral oil;

upstream raw materials:

trans-tert-butyl 4-hydroxycyclohexylcarbamate

ethyl (2-oxocyclopentyl)acetate

ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate

ethyl 2-[12-hydroxy-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]acetate

Downstream raw materials:

2-[(3S)-12-[[4-(dimethylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraen-3-yl]ethan-1-ol

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