(1R,4R)-4-(Boc-amino)cyclopent-2-enecarboxylic acid

Base Information

• Chemical Name: (1R,4R)-4-(Boc-amino)cyclopent-2-enecarboxylic acid
• CAS No.: 298716-03-7
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.26
• Hs Code.: 2924299090
• European Community (EC) Number: 871-730-2
• Nikkaji Number: J2.000.228J
• Mol file: 298716-03-7.mol

Synonyms:298716-03-7;(1R,4R)-4-(Boc-amino)cyclopent-2-enecarboxylic acid;(1R,4R)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid;(1R,4R)-4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylic acid;1212306-65-4;(1R,4R)-4-((tert-butoxycarbonyl)amino)cyclopent-2-ene-1-carboxylic acid;(1R,4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-2-ene-1-carboxylic acid;(1R,4R)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid;MFCD12405610;(1R,4R)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-2-ene-1-carboxylic acid;SCHEMBL1078254;WOUNTSATDZJBLP-YUMQZZPRSA-N;AKOS005145889;AKOS015838064;AM20120599;CS-0093450;A820086;trans-4-Boc-amino-2-cyclopentene-1-carboxylic acid;rel-(1R,4R)-4-(Boc-Amino)cyclopent-2-enecarboxylic acid;trans-(1R,4R)-4-Boc-amino-2-cyclopentene-1-carboxylic acid;(1R,4R)-4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylic acid;(1R,4R)-4-(tert-Butyloxycarbonylamino)-2-cyclopentene-1-carboxylic acid

Chemical Property of (1R,4R)-4-(Boc-amino)cyclopent-2-enecarboxylic acid

Chemical Property:

• Boiling Point: 382.3±42.0 °C(Predicted)
• PKA: 4.31±0.40(Predicted)
• PSA: 75.63000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 1.93130
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 316

Purity/Quality:

98% ^*data from raw suppliers

(1R,4R)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CC(C=C1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H]1C[C@H](C=C1)C(=O)O

Technology Process of (1R,4R)-4-(Boc-amino)cyclopent-2-enecarboxylic acid

There total 9 articles about (1R,4R)-4-(Boc-amino)cyclopent-2-enecarboxylic 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: 22.0%

→ (1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid (151907-79-8,108999-93-5) + (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate (168683-02-1) + (1R,4R)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid (298716-03-7,108999-93-5)

Guidance literature:

With lipase type VII; In phosphate buffer; at 26 ℃; for 24h; pH=7;

DOI:10.1016/j.tet.2003.10.116

Reference yield:

(1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate (168683-02-1) → C11H17NO4 (1312161-65-1) + (1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid (151907-79-8,108999-93-5) + (1R,4R)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid (298716-03-7,108999-93-5)

Guidance literature:

(1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate; With sodium methylate; In methanol; at 0 ℃; for 0.833333h; Industry scale;

With lithium hydrochloride monohydrate; water; In methanol; tert-butyl methyl ether; at -3.5 - 10 ℃; for 22h; Industry scale; Inert atmosphere;

With hydrogenchloride; In methanol; tert-butyl methyl ether; water; pH=3; Industry scale;

Reference yield:

(–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride (229613-83-6,426226-35-9) → C11H17NO4 (1312161-65-1) + (1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid (151907-79-8,108999-93-5) + (1R,4R)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid (298716-03-7,108999-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 19.5 h / 0 - 20 °C / Industry scale; Inert atmosphere

2.1: sodium methylate / methanol / 0.83 h / 0 °C / Industry scale

2.2: 22 h / -3.5 - 10 °C / Industry scale; Inert atmosphere

2.3: pH 3 / Industry scale

With sodium methylate; triethylamine; In methanol; dichloromethane;

upstream raw materials:

(–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride

(1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate

tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

Downstream raw materials:

((1S,2S,4R)-4-(4-(((S)-2,3-dihydro-1H-inden-1-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxycyclopentyl)-methyl sulfamate

(1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(hydroxymethyl)-cyclopentanol

Refernces

• 1、 -. "Process for the synthesis of E1 activating enzyme inhibitors". Page/Page column 30. . Retrieved 2009/03/07.