(S)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid

Base Information

• Chemical Name: (S)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid
• CAS No.: 868689-63-8
• Molecular Formula: C10H17NO5
• Molecular Weight: 231.25
• Hs Code.: 2934999090
• European Community (EC) Number: 841-866-7
• DSSTox Substance ID: DTXSID40364017
• Nikkaji Number: J2.595.685K
• Wikidata: Q72510328
• Mol file: 868689-63-8.mol

Synonyms:868689-63-8;(S)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid;(S)-4-Boc-Morpholine-2-carboxylic acid;(S)-N-Boc-2-morpholinecarboxylic acid;(S)-N-Boc-Morpholine-2-carboxylic acid;(S)-Morpholine-2,4-dicarboxylic acid 4-tert-butyl ester;(2S)-4-[(2-methylpropan-2-yl)oxycarbonyl]morpholine-2-carboxylic acid;(2S)-4-[(TERT-BUTOXY)CARBONYL]MORPHOLINE-2-CARBOXYLIC ACID;MFCD06200662;SCHEMBL194710;(2S)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid;DTXSID40364017;AMY21706;AKOS016842285;AC-4301;CS-W019899;SS-4389;(S)-4-Boc-Morpholine-2-carboxylicacid;(S)-N-Boc-2-morpholine carboxylic acid;EN300-159830;(S)-4-tert-butyloxycarbonyl-2-morpholinecarboxylic acid;(2S)-4-(tert-Butoxycarbonyl)morpholine-2alpha-carboxylic acid;(2S)-2,4-Morpholinedicarboxylic Acid-4-(1,1-Dimethylethyl)ester;(2S)-4-{[(2-Methyl-2-propanyl)oxy]carbonyl}-2-morpholinecarboxylic acid

Chemical Property of (S)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.8E-06mmHg at 25°C
• Melting Point: 127-134 °C
• Refractive Index: 1.492
• Boiling Point: 369.5 °C at 760 mmHg
• PKA: 3.25±0.20(Predicted)
• Flash Point: 177.3 °C
• PSA: 76.07000
• Density: 1.23 g/cm³
• LogP: 0.64480
• Storage Temp.: 2-8°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 231.11067264
• Heavy Atom Count: 16
• Complexity: 283

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-4-(tert-Butoxycarbonyl)morpholine-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCOC(C1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCO[C@@H](C1)C(=O)O
• Uses: (S)-4-(tert-Butoxycarbonyl)morpholine-2-carboxylic Acid can be used for cancer treatment.

Technology Process of (S)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid

There total 2 articles about (S)-4-(tert-butoxycarbonyl)morpholine-2-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: 100.0%

(S)-4-benzyl-morpholine-2-carboxylic acid (1030837-49-0,1260610-90-9) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2,4-morpholinedicarboxylic acid 4-(1,1-dimethylethyl)ester (868689-63-8)

Guidance literature:

With 2,5-dihydrotoluene; 10% Pd on charcoal; In ethanol; Reflux;

DOI:10.1016/j.tetlet.2008.11.025

Reference yield:

tert-butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate (135065-76-8) → (S)-2,4-morpholinedicarboxylic acid 4-(1,1-dimethylethyl)ester (868689-63-8)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutyl-ammonium chloride; potassium bromide;

DOI:10.1016/j.bmcl.2008.09.007

Reference yield: 100.0%

(S)-2,4-morpholinedicarboxylic acid 4-(1,1-dimethylethyl)ester (868689-63-8) → tert-butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate (135065-76-8)

Guidance literature:

With diborane; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

upstream raw materials:

tert-butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate

(S)-4-benzyl-morpholine-2-carboxylic acid

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate

(S)-(+)-2-formylmorpholine-4-carboxylic acid tert-butyl ester

C₁₁H₂₂N₂O₃

benzyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate

Refernces

• 1、 Fish, Paul V.,Mackenny, Malcolm,Bish, Gerwyn,Buxton, Timothy,Cave, Russell,Drouard, David,Hoople, David,Jessiman, Alan,Miller, Duncan,Pasquinet, Christelle,Patel, Bhairavi,Reeves, Keith,Ryckmans, Thomas,Skerten, Melanie,Wakenhut, Florian. "Enantioselective synthesis of (R)- and (S)-N-Boc-morpholine-2-carboxylic acids by enzyme-catalyzed kinetic resolution: application to the synthesis of reboxetine analogs". scheme or table. p. 389 - 391. Retrieved 2009/05/11.
• 2、 Fish, Paul V.,Deur, Christopher,Gan, Xinmin,Greene, Keri,Hoople, David,Mackenny, Malcolm,Para, Kimberly S.,Reeves, Keith,Ryckmans, Thomas,Stiff, Cory,Stobie, Alan,Wakenhut, Florian,Whitlock, Gavin A.. "Design and synthesis of morpholine derivatives. SAR for dual serotonin & noradrenaline reuptake inhibition". . p. 2562 - 2566. Retrieved 2008/12/21.