2-{[tert-Butoxy(hydroxy)methylidene]amino}-2,3-dihydro-1H-indene-2-carboxylate

Base Information

• Chemical Name: 2-{[tert-Butoxy(hydroxy)methylidene]amino}-2,3-dihydro-1H-indene-2-carboxylate
• CAS No.: 71066-00-7
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.32
• Hs Code.: 29224999
• DSSTox Substance ID: DTXSID90991352
• Wikidata: Q82981067
• Mol file: 71066-00-7.mol

Synonyms:DTXSID90991352;2-{[tert-Butoxy(hydroxy)methylidene]amino}-2,3-dihydro-1H-indene-2-carboxylate

Chemical Property of 2-{[tert-Butoxy(hydroxy)methylidene]amino}-2,3-dihydro-1H-indene-2-carboxylate

Chemical Property:

• Appearance/Colour: white to beige crystals or powder
• Vapor Pressure: 3.96E-09mmHg at 25°C
• Refractive Index: 1.5080 (estimate)
• Boiling Point: 456.6 °C at 760 mmHg
• PKA: 3.88±0.20(Predicted)
• Flash Point: 229.9 °C
• PSA: 75.63000
• Density: 1.1311 (rough estimate)
• LogP: 2.52420
• Storage Temp.: 0-6°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 276.12358306
• Heavy Atom Count: 20
• Complexity: 380

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-2-aminoindane-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 24/25-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1(CC2=CC=CC=C2C1)C(=O)[O-]
• Uses: N-Boc-2-aminoindane-2-carboxylic Acid is used to prepare thiol dipeptides as dual inhibitors of angiotensin-I-converting enzyme and neutral endopeptidase.It is also used in the synthesis of bombesin analogs.

Technology Process of 2-{[tert-Butoxy(hydroxy)methylidene]amino}-2,3-dihydro-1H-indene-2-carboxylate

There total 9 articles about 2-{[tert-Butoxy(hydroxy)methylidene]amino}-2,3-dihydro-1H-indene-2-carboxylate 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: 93.0%

ethyl 2-[(N-carbo-2,2-dimethylethoxy)amino]indan-2-carboxylate (255906-25-3) → 2-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-2-carboxylic acid (71066-00-7)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 24h;

DOI:10.1016/S0040-4020(99)00925-4

Reference yield: 48.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-amino-2,3-dihydro-1H-indene-2-carboxylic acid (27473-62-7) → 2-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-2-carboxylic acid (71066-00-7)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 12h;

Reference yield:

2-indanone (615-13-4) → 2-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-2-carboxylic acid (71066-00-7)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium carbonate / aq. ethanol / 55 - 60 °C

2: aq. NaOH / 72 h / Heating

3: aq. NaOH / dioxane / 12 h / Ambient temperature

With ammonium carbonate; sodium hydroxide; In 1,4-dioxane; ethanol;

DOI:10.1021/ja962905b

upstream raw materials:

di-tert-butyl dicarbonate

2-amino-2,3-dihydro-1H-indene-2-carboxylic acid

ethyl 2-[(N-carbo-2,2-dimethylethoxy)amino]indan-2-carboxylate

ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate

Downstream raw materials:

N-{[4-(aminomethyl)phenyl]carbonylamino}{2-[(tert-butoxy)carbonylamino]indan-2-yl}carboxamide

C₃₆H₅₀N₆O₆

Refernces

• 1、 -. "PEPTIDYL NITRILCOMPOUNDS AS PEPTIDASE INHIBITORS". Page/Page column 110. . Retrieved 2012/09/22.
• 2、 Williams, Lawrence J.,Jagadish,Lyon, Scott R.,Kloster, Robin A.,Carducci, Michael D.,Mash, Eugene A.. "Organic crystal engineering with piperazine-2,5-diones. 1. Crystal packing of piperazinediones derived from substituted 2-aminoindan-2- carboxylic acids". . p. 14281 - 14300. Retrieved 2007/10/03.