(R)-2-Amino-3-(4-bromo-1H-indol-3-yl)propanoic acid

Base Information

• Chemical Name: (R)-2-Amino-3-(4-bromo-1H-indol-3-yl)propanoic acid
• CAS No.: 219943-61-0
• Molecular Formula: C11H11BrN2O2
• Molecular Weight: 283.12
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID90444494
• Nikkaji Number: J1.060.007C
• Mol file: 219943-61-0.mol

Synonyms:219943-61-0;(R)-2-Amino-3-(4-bromo-1H-indol-3-yl)propanoic acid;4-BROMO-D-TRYPTOPHAN;(2R)-2-AMINO-3-(4-BROMO-1H-INDOL-3-YL)PROPANOIC ACID;(R)-2-Amino-3-(4-bromo-1H-indol-3-yl)propanoicacid;DTXSID90444494;AKOS016008161;CS-0449684

Chemical Property of (R)-2-Amino-3-(4-bromo-1H-indol-3-yl)propanoic acid

Chemical Property:

• Melting Point: 288-290 °C
• Boiling Point: 495.8±45.0 °C(Predicted)
• PKA: 2.19±0.10(Predicted)
• PSA: 79.11000
• Density: 1.704±0.06 g/cm3(Predicted)
• LogP: 2.58510
• Storage Temp.: 2-8°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 282.00039
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

98.5% ^*data from raw suppliers

(R)-2-Amino-3-(4-bromo-1H-indol-3-yl)propanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)Br)C(=CN2)CC(C(=O)O)N
• Isomeric SMILES: C1=CC2=C(C(=C1)Br)C(=CN2)C[C@H](C(=O)O)N

Technology Process of (R)-2-Amino-3-(4-bromo-1H-indol-3-yl)propanoic acid

There total 14 articles about (R)-2-Amino-3-(4-bromo-1H-indol-3-yl)propanoic 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: 92.0%

(R)-4-bromo-N-(tert-butoxycarbonyl)tryptophan methyl ester → (R)-4-bromotryptophan (219943-61-0)

Guidance literature:

With water; silica gel; at 140 ℃; for 20h; Reagent/catalyst; enantioselective reaction;

DOI:10.1016/j.tetlet.2020.151923

Reference yield:

(S)-4-bromo-N-(tert-butoxycarbonyl)tryptophan methyl ester (691885-32-2) → (R)-4-bromotryptophan (219943-61-0) + (S)-2-amino-3-(4-bromo-1H-indol-3-yl)propanoic acid (52448-16-5)

Guidance literature:

(S)-4-bromo-N-(tert-butoxycarbonyl)tryptophan methyl ester; With potassium hydroxide; water; In 1,4-dioxane; at 20 ℃; for 1.5h;

With water; acetic acid; at 80 ℃; for 3h; Further stages.;

DOI:10.1002/ejoc.200300603

Reference yield:

4-bromo-1H-indole (52488-36-5) → (R)-4-bromotryptophan (219943-61-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 31.0 g / pyridinium bromide perbromide / pyridine / 0.25 h / 0 °C

2: Et₃N, DMAP / tetrahydrofuran / 14 h

3: 1.) n-BuLi / 1.) THF, -78 deg C, 90 min, 2.) THF, -75 deg C, 4 h

4: 99 percent / NaOMe / tetrahydrofuran / 1 h / Ambient temperature

5: 91 percent / DMAO, BH₃*THF / tetrahydrofuran / 72 h / 0 °C

6: 95 percent / DMAP / tetrahydrofuran / 4 h / Ambient temperature

7: 86 percent / 1M HCl / ethyl acetate / 1.) 0 deg C to room temperature, 1 h, 2.) room temperature, 4 h

8: 1.) NCS, DMS, 2.) Et₃N / 1.) toluene, -25 deg C, 6 h, 2.) -25 deg C, 10 min; room temperature, 1 h

9: 69 percent / 2-methyl-2-butene, NaClO₂, NaH₂PO₄ / acetonitrile; 2-methyl-propan-2-ol; H₂O / 0.17 h / 0 °C

10: 1.) Et₃SiH, TMSOTf, 2.) 1M HCl / 1.) DCE, reflux, 1 h, 2.) reflux, 2 h

With hydrogenchloride; triethylsilane; dmap; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; n-butyllithium; borane-THF; 2-methyl-but-2-ene; 2,3-dimercapto-succinic acid; trimethylsilyl trifluoromethanesulfonate; sodium methylate; pyridinium hydrobromide perbromide; triethylamine; In tetrahydrofuran; pyridine; water; ethyl acetate; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo981723s

upstream raw materials:

(R)-4-bromo-1-(tert-butyloxycarbonyl)-α-N-(9-phenyl-9-fluorenyl)tryptophan

(S)-4-bromo-N-(tert-butoxycarbonyl)tryptophan methyl ester

(S)-4-bromo-N-(tert-butoxycarbonyl)-1-tosyltryptophan methyl ester

4-bromo-1H-indole

Downstream raw materials:

(R)-4-bromo-α-N-trityltryptophan trityl ester

(R)-4-bromo-α-N-trityltryptophan

(R)-4-bromo-α-N-trityltryptophan methyl ester