TERT-BUTYL TRANS-4-(N-METHOXY-N-METHYLCARBAMOYL)CYCLOHEXYLCARBAMATE

Base Information

• Chemical Name: TERT-BUTYL TRANS-4-(N-METHOXY-N-METHYLCARBAMOYL)CYCLOHEXYLCARBAMATE
• CAS No.: 400898-92-2
• Molecular Formula: C14H26N2O4
• Molecular Weight: 286.371
• Hs Code.: 2924299090
• Mol file: 400898-92-2.mol

Synonyms:TERT-BUTYL TRANS-4-(N-METHOXY-N-METHYLCARBAMOYL)CYCLOHEXYLCARBAMATE;Carbamic acid, [trans-4-[(methoxymethylamino)carbonyl]cyclohexyl]-, 1,1-dimethylethyl ester (9CI);trans-1-(Boc-aMino)-4-(N-Methoxy-N-MethylcarbaMoyl)cyclohexane, 97%

Chemical Property of TERT-BUTYL TRANS-4-(N-METHOXY-N-METHYLCARBAMOYL)CYCLOHEXYLCARBAMATE

Chemical Property:

• PKA: 12.27±0.40(Predicted)
• PSA: 67.87000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 2.48060

Purity/Quality:

99%+, ^*data from raw suppliers

tert-Butyl trans-4-(N-methoxy-N-methylcarbamoyl)-cyclohexylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TERT-BUTYL TRANS-4-(N-METHOXY-N-METHYLCARBAMOYL)CYCLOHEXYLCARBAMATE

There total 3 articles about TERT-BUTYL TRANS-4-(N-METHOXY-N-METHYLCARBAMOYL)CYCLOHEXYLCARBAMATE 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: 100.0%

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid (53292-90-3,130309-46-5,53292-89-0) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → trans-[4-(methoxymethylcarbamoyl)cyclohexyl]carbamic acid tert-butyl ester (400898-92-2)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm300256z

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → trans-[4-(methoxymethylcarbamoyl)cyclohexyl]carbamic acid tert-butyl ester (400898-92-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 1,4-dioxane; water / 2 h / 0 - 20 °C

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In 1,4-dioxane; dichloromethane; water;

DOI:10.1021/acsmedchemlett.0c00443

Reference yield:

trans-4-aminocyclohexanecarboxylic acid (1776-53-0,3685-23-2,3685-25-4,57043-03-5,66762-20-7) → trans-[4-(methoxymethylcarbamoyl)cyclohexyl]carbamic acid tert-butyl ester (400898-92-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / 1,4-dioxane; water / 2 h / 0 - 20 °C

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In 1,4-dioxane; dichloromethane; water;

DOI:10.1021/acsmedchemlett.0c00443

upstream raw materials:

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid

N,O-dimethylhydroxylamine*hydrochloride

di-tert-butyl dicarbonate

trans-4-aminocyclohexanecarboxylic acid

Downstream raw materials:

trans-N-[4-(N-methoxy-N-methylcarbamoyl)cyclohexyl]-N-methylcarbamic acid tert-butyl ester

trans-[4-(2,2-dibromovinyl)cyclohexyl]-N-methylcarbamic acid tert-butyl ester

trans-(4-formylcyclohexyl)methylcarbamic acid tert-butyl ester

Refernces

• 1、 Jin, Fangfang,Hu, Qiyue,Fei, Hongbo,Lv, Hejun,Wang, Shenglan,Gui, Bin,Zhang, Junzhen,Tu, Wangyang,Zhang, Yun,Zhang, Lei,Wan, Hong,Zhang, Limin,Hu, Bin,Yang, Fanglong,Bai, Chang,He, Feng,Zhang, Lianshan,Tao, Weikang. "Discovery of Hydroxyamidine Derivatives as Highly Potent, Selective Indoleamine-2,3-dioxygenase 1 Inhibitors". supporting information. p. 195 - 201. Retrieved 2021/02/06.