(S)-1-(tert-Butoxycarbonyl)indoline-2-carboxylic acid

Base Information

• Chemical Name: (S)-1-(tert-Butoxycarbonyl)indoline-2-carboxylic acid
• CAS No.: 144069-67-0
• Molecular Formula: C14H17 N O4
• Molecular Weight: 263.293
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID00373160
• Nikkaji Number: J1.459.205I
• Mol file: 144069-67-0.mol

Synonyms:144069-67-0;(S)-1-(tert-Butoxycarbonyl)indoline-2-carboxylic acid;Boc-L-indoline-2-carboxylic acid;(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-2,3-dihydroindole-2-carboxylic acid;(2S)-1-(tert-butoxycarbonyl)-2,3-dihydro-1H-indole-2-carboxylic acid;(2S)-1-[(tert-butoxy)carbonyl]-2,3-dihydro-1H-indole-2-carboxylic acid;Boc-L-Idc-OH;MFCD00273433;BOC-(S)-(-)-INDOLINE-2-CARBOXYLIC ACID;SCHEMBL927332;(S)-1-(tert-Butoxycarbonyl)indoline-2-carboxylicacid;DTXSID00373160;QONNUMLEACJFME-NSHDSACASA-N;AKOS015911607;FS-5103;N-Boc-(S)-indoline-2-carboxylic acid;CS-0207686;EN300-52857;Boc-(2S)-indoline carboxylic acid, AldrichCPR;E86396;(S)-N-tert-butoxycarbonylindoline-2-carboxylic acid;(2S)-1-(tert-Butoxycarbonyl)indoline-2-carboxylic acid;(R)-N-alpha-t-Butyloxycarbonyl-2-indolinecarboxylic acid;(S)-2,3-Dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester;(S)-N-ALPHA-T-BUTYLOXYCARBONYL-2-INDOLINECARBOXYLIC ACID

Chemical Property of (S)-1-(tert-Butoxycarbonyl)indoline-2-carboxylic acid

Chemical Property:

• PSA: 66.84000
• LogP: 2.50240
• Storage Temp.: Store at 0°C
• XLogP3: 2.3
• 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%min ^*data from raw suppliers

Boc-L-indoline-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C(CC2=CC=CC=C21)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@@H](CC2=CC=CC=C21)C(=O)O

Technology Process of (S)-1-(tert-Butoxycarbonyl)indoline-2-carboxylic acid

There total 13 articles about (S)-1-(tert-Butoxycarbonyl)indoline-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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-indoline-2-carboxylic acid (79815-20-6,78348-24-0) → (S)-N-tert-butoxycarbonylindoline-2-carboxylic acid (144069-67-0,133851-52-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2005.07.040

Reference yield: 49.0%

methyl (+/-)-1-t-butoxycarbonyl-indoline-2-carboxylate (186704-03-0) → (S)-N-tert-butoxycarbonylindoline-2-carboxylic acid (144069-67-0,133851-52-2) + methyl (R)-N-(tert-butoxycarbonyl)indoline-2-carboxylate (158457-36-4)

Guidance literature:

With Chirazyme L-2; In phosphate buffer; at 60 ℃; for 30h; pH=7.0;

DOI:10.1246/bcsj.77.1021

Reference yield:

aniline (62-53-3) → (S)-N-tert-butoxycarbonylindoline-2-carboxylic acid (144069-67-0,133851-52-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: HCl; NaNO₂ / H₂O / 0.25 h / 0 °C

1.2: 63 percent / KOH / ethanol; H₂O / 15 h / 0 - 4 °C / pH 6.0

2.1: 732 mg / acetic acid / H₂O / 15 h / 20 °C

3.1: 85 percent / HBr / acetic acid / 2 h / 20 °C

4.1: DBU / 3 h / Heating

5.1: 99 percent / 4-dimethylaminopyridine / tetrahydrofuran / 1 h / 20 °C

6.1: 92 percent / magnesium; methanol / 4 h / 0 °C

7.1: 49 percent / Chirazyme L-2 / aq. phosphate buffer / 30 h / 60 °C / pH 7.0

With hydrogenchloride; methanol; dmap; Chirazyme L-2; hydrogen bromide; magnesium; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium nitrite; In tetrahydrofuran; phosphate buffer; water; acetic acid; 1.2: Japp-Klingemann azo ester synthesis / 2.1: retro-Claisen condensation / 3.1: Fischer indole cyclization;

DOI:10.1246/bcsj.77.1021

upstream raw materials:

di-tert-butyl dicarbonate

(S)-indoline-2-carboxylic acid

methyl (+/-)-1-t-butoxycarbonyl-indoline-2-carboxylate

indole-2-carboxylic acid methyl ester

Refernces

• 1、 Hayashi, Shigeo,Ohashi, Katsuyo,Nakata, Eriko,Emoto, Chie. "Discovery of 1-(β-amino substituted-β-alanyl)-N,N- dimethylindoline-2-carboxamides as novel nonpeptide antagonists of nociceptin/orphanin FQ receptor: Efficient design, synthesis, and structure-activity relationship studies". . p. 228 - 242. Retrieved 2012/11/07.
• 2、 -. "AMIDO ANTI-VIRAL COMPOUNDS". Page/Page column 82-83. . Retrieved 2008/12/05.