(1R,2S)-2-(phenylmethoxycarbonylamino)cyclohexane-1-carboxylic acid

Base Information

• Chemical Name: (1R,2S)-2-(phenylmethoxycarbonylamino)cyclohexane-1-carboxylic acid
• CAS No.: 202867-96-7
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.32
• DSSTox Substance ID: DTXSID101159075
• Mol file: 202867-96-7.mol

Synonyms:54867-08-2;Z-1,2-cis-ACHC-OH;(1R,2S)-2-(phenylmethoxycarbonylamino)cyclohexane-1-carboxylic acid;cis-2-(benzyloxycarbonylamino)cyclohexanecarboxylic acid;(1R,2S)-2-{[(BENZYLOXY)CARBONYL]AMINO}CYCLOHEXANE-1-CARBOXYLIC ACID;cis-2-(((Benzyloxy)carbonyl)amino)cyclohexanecarboxylic acid;202867-96-7;SCHEMBL6200837;RPJMLWMATNCSIS-OLZOCXBDSA-N;DTXSID101159075;MFCD01863245;EN300-737690;EN300-19627074;A1-51431;cis-2-(((Benzyloxy)carbonyl)amino)cyclohexanecarboxylicacid;Cis-(+/-)-2-benzyloxycarbonylaminocyclohexanecarboxylic acid;CIS-1-(BENZYLOXYCARBONYL-AMINO)-CYCLOHEXYL-2-CARBOXYLIC ACID;(1R,2S)-2-[[(Phenylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid;rac-(1R,2S)-2-{[(benzyloxy)carbonyl]amino}cyclohexane-1-carboxylic acid

Chemical Property of (1R,2S)-2-(phenylmethoxycarbonylamino)cyclohexane-1-carboxylic acid

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 277.13140809
• Heavy Atom Count: 20
• Complexity: 339

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC(C(C1)C(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1CC[C@@H]([C@@H](C1)C(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of (1R,2S)-2-(phenylmethoxycarbonylamino)cyclohexane-1-carboxylic acid

There total 9 articles about (1R,2S)-2-(phenylmethoxycarbonylamino)cyclohexane-1-carboxylic acid 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: 82.0%

(2-acetyl-cyclohexyl)-carbamic acid benzyl ester (541522-70-7) → 2-benzyloxycarbonylamino-cyclohexanecarboxylic acid (202867-96-7)

Guidance literature:

(2-acetyl-cyclohexyl)-carbamic acid benzyl ester; With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 24h;

With hydrogenchloride; In tetrahydrofuran; water; at 0 ℃;

Reference yield:

(1R,2S)-2-Benzyloxycarbonylamino-cyclohexane-1-carboxylic acid methyl ester (202867-95-6) → 2-benzyloxycarbonylamino-cyclohexanecarboxylic acid (202867-96-7)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/S0960-894X(98)00200-5

Reference yield:

cis-2-aza-3-oxobicyclo<4.2.0>octane (22031-53-4,34102-49-3,150781-24-1) → 2-benzyloxycarbonylamino-cyclohexanecarboxylic acid (202867-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: HCl

2.1: Na₂CO₃ / dioxane

2.2: chiral HPLC

With hydrogenchloride; sodium carbonate; In 1,4-dioxane; 1.1: Ring cleavage / 2.1: Acylation / 2.2: racemate resolution;

DOI:10.1016/S0960-894X(00)00475-3

upstream raw materials:

(1R,2S)-2-Benzyloxycarbonylamino-cyclohexane-1-carboxylic acid methyl ester

benzyl chloroformate

(±)-cis-2-aminocyclohexane-1-carboxylic acid hydrochloride

cis-2-aza-3-oxobicyclo<4.2.0>octane

Downstream raw materials:

C₂₆H₃₁ClN₂O₄

(1R,2S)-2-[(R)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-cyclohexanecarboxylic acid

C₃₉H₄₈N₆O₇

((R)-1-{(1S,2R)-2-[(S)-1-(Benzyloxycarbonylamino-imino-methyl)-2-oxo-piperidin-3-ylcarbamoyl]-cyclohexylcarbamoyl}-2-phenyl-ethyl)-methyl-carbamic acid benzyl ester