Tert-butoxycarbonylamino-O-tolyl-acetic acid

Base Information

• Chemical Name: Tert-butoxycarbonylamino-O-tolyl-acetic acid
• CAS No.: 40512-48-9
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.309
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID00960918
• Nikkaji Number: J3.454.077B
• Mol file: 40512-48-9.mol

Synonyms:40512-48-9;TERT-BUTOXYCARBONYLAMINO-O-TOLYL-ACETIC ACID;2-{[(tert-butoxy)carbonyl]amino}-2-(2-methylphenyl)acetic acid;2-(2-methylphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid;2-((tert-Butoxycarbonyl)amino)-2-(o-tolyl)acetic acid;boc-dl-(2-methylphenyl)glycine;2-(tert-butoxycarbonylamino)-2-o-tolylacetic acid;SCHEMBL15270465;DTXSID00960918;1004759-89-0;1228565-65-8;MFCD03789594;AKOS013464355;AB32651;AB32652;AS-71429;CS-0215121;EN300-224974;W18587;2-((tert-Butoxycarbonyl)amino)-2-(o-tolyl)aceticacid;tert-Butoxycarbonylamino-o-tolyl-acetic acid, AldrichCPR;Z1200998673;{[tert-Butoxy(hydroxy)methylidene]amino}(2-methylphenyl)acetic acid;(2R)-2-[(TERT-BUTOXY)CARBONYLAMINO]-2-(2-METHYLPHENYL)ACETIC ACID;(2S)-2-[(TERT-BUTOXY)CARBONYLAMINO]-2-(2-METHYLPHENYL)ACETIC ACID;2-((t-Butoxycarbonyl)amino)-2-(o-tolyl)acetic acid (Boc-DL-Phg(2-Me)-OH)

Chemical Property of Tert-butoxycarbonylamino-O-tolyl-acetic acid

Chemical Property:

• Boiling Point: 423.6±40.0 °C(Predicted)
• PKA: 3.51±0.10(Predicted)
• PSA: 75.63000
• Density: 1.159±0.06 g/cm3(Predicted)
• LogP: 3.03630
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

98%min ^*data from raw suppliers

Boc-DL-(2-methylphenyl)glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C(C(=O)O)NC(=O)OC(C)(C)C

Technology Process of Tert-butoxycarbonylamino-O-tolyl-acetic acid

There total 3 articles about Tert-butoxycarbonylamino-O-tolyl-acetic 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: 80.0%

N-(tert-butoxycarbonyl)-α-(phenylsulfonyl)-2-methylbenzylamine (479423-25-1) + carbon dioxide (124-38-9,18923-20-1) → 2-(tert-butoxycarbonylamino)-2-(2-methylphenyl)acetic acid (40512-48-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 0 ℃; under 760.051 Torr; Electrochemical reaction;

DOI:10.1021/acs.joc.1c01516

Reference yield: 73.0%

(S)-2-(tert-butoxycarbonylamino)-2-(2-methylphenyl)ethanol (1004759-88-9) → N-Boc-(2-methylphenyl)glycine (1004759-89-0,40512-48-9)

Guidance literature:

With ruthenium trichloride; sodium periodate; In water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2010.09.105

Reference yield:

(S)-α-amino-α-o-tolylacetic acid hydrochloride (1004980-56-6) + di-tert-butyl dicarbonate (24424-99-5) → N-Boc-(2-methylphenyl)glycine (1004759-89-0,40512-48-9)

Guidance literature:

With sodium hydrogencarbonate; In water; tert-butyl alcohol; for 5h;

DOI:10.1016/j.tet.2009.04.098

upstream raw materials:

(S)-2-(tert-butoxycarbonylamino)-2-(2-methylphenyl)ethanol

(S)-α-amino-α-o-tolylacetic acid hydrochloride

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)-α-(phenylsulfonyl)-2-methylbenzylamine

Downstream raw materials:

(S)-methyl 2-((tert-butoxycarbonyl)amino)-2-(o-tolyl)acetate

Refernces

• 1、 Tayama, Eiji,Takedachi, Keisuke,Iwamoto, Hajime,Hasegawa, Eietsu. "Remarkable enhancement effect of potassium tert-butoxide/THF solution in base-induced Sommelet-Hauser rearrangements". supporting information; experimental part. p. 9389 - 9395. Retrieved 2011/01/12.
• 2、 Tayama, Eiji,Kimura, Hiroshi. "Asymmetric Sommelet-Hauser rearrangement of N-benzylic ammonium salts". . p. 8869 - 8871. Retrieved 2008/09/19.