tert-butyl N-(4-[[(3R)-3-(2-hydroxypropyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-12-yl]amino]cyclohexyl)carbamate

Base Information

• Chemical Name: tert-butyl N-(4-[[(3R)-3-(2-hydroxypropyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-12-yl]amino]cyclohexyl)carbamate
• CAS No.: 1388894-28-7
• Molecular Formula: C₂₃H₃₄N₄O₃S
• Molecular Weight: 446.614

Synonyms:tert-butyl N-(4-[[(3R)-3-(2-hydroxypropyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-12-yl]amino]cyclohexyl)carbamate

Chemical Property of tert-butyl N-(4-[[(3R)-3-(2-hydroxypropyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-12-yl]amino]cyclohexyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of tert-butyl N-(4-[[(3R)-3-(2-hydroxypropyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-12-yl]amino]cyclohexyl)carbamate

There total 8 articles about tert-butyl N-(4-[[(3R)-3-(2-hydroxypropyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-12-yl]amino]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: 42.0%

tert-butyl N-(4-[[(3R)-3-(2-oxoethyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1(8),2(6),9,11-tetraen-12-yl]amino]cyclohexyl)carbamate (1388894-07-2) + methylmagnesium bromide (75-16-1) → tert-butyl N-(4-[[(3R)-3-(2-hydroxypropyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1(8),2(6),9,11-tetraen-12-yl]amino]cyclohexyl)carbamate (1388894-28-7)

Guidance literature:

tert-butyl N-(4-[[(3R)-3-(2-oxoethyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-12-yl]amino]cyclohexyl)carbamate; methylmagnesium bromide; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; Inert atmosphere;

Reference yield:

trans-N-Boc-1,4-cyclohexanediamine (177906-48-8) → tert-butyl N-(4-[[(3R)-3-(2-hydroxypropyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1(8),2(6),9,11-tetraen-12-yl]amino]cyclohexyl)carbamate (1388894-28-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

1.2: 14 h / 50 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

4.1: tetrahydrofuran / 0 °C / Inert atmosphere

4.2: Inert atmosphere

With tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

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-[[(3R)-3-(2-hydroxypropyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1(8),2(6),9,11-tetraen-12-yl]amino]cyclohexyl)carbamate (1388894-28-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 20 - 180 °C / Inert atmosphere

1.2: Cooling with ice

2.1: trichlorophosphate / 20 - 110 °C

3.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / -30 °C / Inert atmosphere

4.1: CHIRALPAK IA / carbon dioxide; methanol / Resolution of racemate

5.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

6.1: triethylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

6.2: 14 h / 50 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

8.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

9.1: tetrahydrofuran / 0 °C / Inert atmosphere

9.2: Inert atmosphere

With 1H-imidazole; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol; hexane; dichloromethane; carbon dioxide; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyl N-(4-[[(3R)-3-(2-oxoethyl)-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-12-yl]amino]cyclohexyl)carbamate

methylmagnesium bromide

trans-N-Boc-1,4-cyclohexanediamine

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

Downstream raw materials:

1-[(3R)-12-[(4-aminocyclohexyl)amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]propan-2-ol

(2S)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]propan-2-ol formate

(2R)-1-[(3R)-12-[[4-(dimethylamino)cyclohexyl]amino]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]propan-2-ol formate

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