Trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride

Base Information

• Chemical Name: Trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride
• CAS No.: 27687-13-4
• Molecular Formula: C16H20ClNO3
• Molecular Weight: 309.793
• DSSTox Substance ID: DTXSID701131015
• Mol file: 27687-13-4.mol

Synonyms:SCHEMBL7333350;SCHEMBL7333353;PPSRARCZQBUQCB-MQMHXKEQSA-N;DTXSID701131015;Trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride;Trans-4-(N-carbobenzyloxy)aminomethyl-l-cyclohexane carbonyl chloride;Carbamic acid, [[4-(chlorocarbonyl)cyclohexyl]methyl]-, phenylmethyl ester, trans-;27687-13-4

Chemical Property of Trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 309.1131712
• Heavy Atom Count: 21
• Complexity: 347

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CCC1CNC(=O)OCC2=CC=CC=C2)C(=O)Cl

Technology Process of Trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride

There total 6 articles about Trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride 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:

(1r,4r)-4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexane-1-carboxylic acid (27687-12-3) → trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride (27687-13-4)

Guidance literature:

With thionyl chloride;

DOI:10.1021/jm00273a011 DOI:10.1248/cpb.39.2340 DOI:10.1248/cpb.39.2930

Reference yield:

trans-4-aminomethyl-cyclohexyl-carboxylic acid (1197-18-8) → trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride (27687-13-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 10percent aq. NaOH / 1 h

2: SOCl₂ / 0.5 h / 40 °C

With sodium hydroxide; thionyl chloride;

DOI:10.1021/jm970389+

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → trans-4-(N-carbobenzyloxy)aminomethyl-1-cyclohexane carbonyl chloride (27687-13-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 10percent aq. NaOH / 1 h

2: SOCl₂ / 0.5 h / 40 °C

With sodium hydroxide; thionyl chloride;

DOI:10.1021/jm970389+

upstream raw materials:

(1r,4r)-4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexane-1-carboxylic acid

trans-4-aminomethyl-cyclohexyl-carboxylic acid

benzyl chloroformate

4-(Benzyloxycarbonylamino-methyl)-cyclohexanecarboxylic acid

Downstream raw materials:

2,3,4,6-tetra-O-acetyl-N-<4-trans-N-(benzyloxycarbonylamino)methylcyclohexylcarbonyl>-β-D-mannopyranosylamine

4-(Benzyloxycarbonylamino-methyl)-cyclohexanecarboxylic acid 2,6-dimethyl-phenyl ester

4-(Benzyloxycarbonylamino-methyl)-cyclohexanecarboxylic acid 4-tert-butyl-phenyl ester

4-(Benzyloxycarbonylamino-methyl)-cyclohexanecarboxylic acid 4-hydroxymethyl-phenyl ester

Refernces

• 1、 -. "Preparation of N-[(indolecarbonyl)cyclohexylmethyl]imidazopyridines as platelet activating factor antagonists.". . . Retrieved 2008/06/13.
• 2、 Teno,Wanaka,Okada,Tsuda,Okamoto,Hijikata-Okunomiya,Naito,Okamoto. "Development of active center-directed inhibitors against plasmin". . p. 2340 - 2346. Retrieved 2007/10/02.