2-(Tert-butoxycarbonyl)isoindoline-1-carboxylic acid

Base Information

• Chemical Name: 2-(Tert-butoxycarbonyl)isoindoline-1-carboxylic acid
• CAS No.: 221352-46-1
• Molecular Formula: C14H17NO4
• Molecular Weight: 263.293
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID60373166
• Mol file: 221352-46-1.mol

Synonyms:221352-46-1;2-(tert-butoxycarbonyl)isoindoline-1-carboxylic acid;1,3-Dihydro-isoindole-1,2-dicarboxylic acid 2-tert-butyl ester;2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-dihydroisoindole-1-carboxylic Acid;Boc-(R,S)-1,3-dihydro-2H-isoindole carboxylic acid;(R,S)-BOC-1,3-DIHYDRO-2H-ISOINDOLE CARBOXYLIC ACID;2-boc-isoindoline-1-carboxylic acid;1,3-Dihydroisoindole-1,2-dicarboxylic acid 2-tert-butyl ester;MFCD01321007;Boc-Disc-OH;2-tert-butoxycarbonylisoindoline-1-carboxylic acid;2-(tert-Butoxycarbonyl)isoindoline-1-carboxylicacid;SCHEMBL205299;DTXSID60373166;BBMCBMREDOQCDU-UHFFFAOYSA-N;1,3-Dihydro-isoindole-1,2-dicarboxylicacid2-tert-butylester;2-(Boc)-1-isoindolinecarboxylic acid;AKOS016001694;AB88388;SB35523;AC-30554;AS-31211;SY066363;A4759;CS-0039846;FT-0649802;EN300-386268;5-Bromo-4-Chloro-2-fluoro-benzoicacidmethylester;N-BOC-1,3-dihydro-2H-isoindol-1-carboxylic acid;(R,S)-Boc-1,3-Dihydro-2H-isoindolecarboxylic acid;J-502305;N-BOC-1,3-dihydro-2H-isoindole-1-carboxylic acid;tert-Butyl 1-(hydroperoxymethyl)isoindoline-2-carboxylate;2-(tert-Butoxycarbonyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid;1,3-Dihydro-isoindole-1,2-dicarboxylic acid 2-tert-butyl ester, AldrichCPR;2-[(tert-butoxy)carbonyl]-2,3-dihydro-1H-isoindole-1-carboxylic acid;racemic 1,3-dihydro-isoindole-1,2-dicarboxylic acid 2-tert-butyl ester

Chemical Property of 2-(Tert-butoxycarbonyl)isoindoline-1-carboxylic acid

Chemical Property:

• Vapor Pressure: 8.4E-08mmHg at 25°C
• Refractive Index: 1.567
• Boiling Point: 419.9 °C at 760 mmHg
• PKA: 3.52±0.20(Predicted)
• Flash Point: 207.8 °C
• PSA: 66.84000
• Density: 1.259g/cm³
• LogP: 2.50090
• Storage Temp.: Store at -15°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 263.11575802
• Heavy Atom Count: 19
• Complexity: 374

Purity/Quality:

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

Boc-(R,S)-1,3-dihydro-2H-isoindolecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC2=CC=CC=C2C1C(=O)O
• Uses: Boc-(R,S)-1,3-dihydro-2H-isoindole carboxylic Acid is used in preparation of biaryls, arylheteroaryls, heteroaryls, biarylacetylenes and related compouns end-capped with amino acid or peptide derivatives as antiviral agents.

Technology Process of 2-(Tert-butoxycarbonyl)isoindoline-1-carboxylic acid

There total 6 articles about 2-(Tert-butoxycarbonyl)isoindoline-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:

1-methoxycarbonylmethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (444583-12-4) → 2-(tert-butoxycarbonyl)isoindoline-1-carboxylic acid (221352-46-1)

Guidance literature:

With lithium hydroxide; water; In methanol; at 20 - 45 ℃; for 18h;

Reference yield:

tert-butyl (+/-)-1-cyano-1,3-dihydro-2H-isoindole-2-carboxylate (1367468-00-5) → 2-(tert-butoxycarbonyl)isoindoline-1-carboxylic acid (221352-46-1)

Guidance literature:

tert-butyl (+/-)-1-cyano-1,3-dihydro-2H-isoindole-2-carboxylate; With water; sodium hydroxide; at 60 ℃; for 3h;

With potassium hydrogensulfate; In water; at 20 ℃;

DOI:10.1021/ol300250h

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + O-tert-butyl 1-(tributylstannyl)isoindoline-2-carboxylate (1359987-44-2) → 2-(tert-butoxycarbonyl)isoindoline-1-carboxylic acid (221352-46-1)

Guidance literature:

carbon dioxide; O-tert-butyl 1-(tributylstannyl)isoindoline-2-carboxylate; With cesium fluoride; In N,N-dimethyl-formamide; at 120 ℃; for 3h; under 7500.75 Torr; Autoclave;

With hydrogenchloride; In diethyl ether; water; N,N-dimethyl-formamide; at 0 ℃; pH=2; Inert atmosphere;

DOI:10.1021/jo202597p

upstream raw materials:

1-methoxycarbonylmethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

carbon dioxide

O-tert-butyl 1-(tributylstannyl)isoindoline-2-carboxylate

tert-butyl (+/-)-1-hydroxy-1,3-dihydro-2H-isoindole-2-carboxylate

Downstream raw materials:

C₂₃H₂₂F₆N₂O₃

2-benzyl 1-methyl (+/-)-1,3-dihydro-2H-isoindole-1,2-dicarboxylate

(+/-)-2-[(benzyloxy)carbonyl]-1,3-dihydro-2H-isoindole-1-carboxylic acid

(R)-2-benzyl 1-methyl 1,3-dihydro-2H-isoindole-1,2-dicarboxylate

Refernces

• 1、 Moran-Ramallal, Roberto,Gotor-Fernandez, Vicente,Laborda, Pedro,Sayago, Francisco J.,Cativiela, Carlos,Gotor, Vicente. "Dynamic kinetic resolution of 1,3-dihydro-2 h-isoindole-1-carboxylic acid methyl ester: Asymmetric transformations toward isoindoline carbamates". . p. 1696 - 1699. Retrieved 2012/06/29.