(S)-3-(Benzo[b]thiophen-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Base Information

• Chemical Name: (S)-3-(Benzo[b]thiophen-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid
• CAS No.: 154902-51-9
• Molecular Formula: C16H19NO4S
• Molecular Weight: 321.39
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90935094
• Wikidata: Q72448618
• Mol file: 154902-51-9.mol

Synonyms:154902-51-9;Boc-L-3-Benzothienylalanine;(S)-3-(Benzo[b]thiophen-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid;Boc-3-(3-benzothienyl)-L-alanine;Boc-beta-(3-benzothienyl)-L-alanine;(2S)-3-(1-benzothiophen-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;Boc-beta-(3-benzothienyl)-Ala-OH;Boc-L-3-Benzothienylala;Boc-Ala(3-Bzt)-OH;SCHEMBL999046;Boc--(3-benzothienyl)-Ala-OH;DTXSID90935094;MURVSBJYXHTRJQ-LBPRGKRZSA-N;MFCD00237538;AKOS015836441;AKOS015948718;Boc- beta -(3-benzothienyl)-Ala-OH;AC-9640;AM83626;CS-W009890;DS-8275;A50218;A809584;J-009158;Boc-beta-(3-benzothienyl)-Ala-OH, >=96.0% (TLC);3-(1-Benzothiophen-3-yl)-N-[tert-butoxy(hydroxy)methylidene]alanine;Boc-L-3-BenZothienylalanine (Boc-L-Ala(benZothiophen-3-yl)-OH);(2s)-3-benzo[b]thiophen-3-yl-2-[(tert-butoxy)carbonylamino]propanoic acid;(S)-3-(Benzo[b]thiophen-3-yl)-2-((tert-butoxycarbonyl)amino)propanoicacid;3-(1-benzothien-3-yl)-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-alanine;(2S)-3-(1-benzothiophen-3-yl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid;Benzo[b]thiophene-3-propanoic acid, alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-, (alphaS)-

Chemical Property of (S)-3-(Benzo[b]thiophen-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Chemical Property:

• Vapor Pressure: 2.56E-09mmHg at 25°C
• Refractive Index: 1.53
• Boiling Point: 514.1 °C at 760 mmHg
• PKA: 3.85±0.10(Predicted)
• Flash Point: 264.7 °C
• PSA: 103.87000
• Density: 1.274 g/cm³
• LogP: 3.81260
• Storage Temp.: -15°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 321.10347926
• Heavy Atom Count: 22
• Complexity: 421

Purity/Quality:

98%min ^*data from raw suppliers

Boc-3-benzothienyl-L-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CSC2=CC=CC=C21)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CSC2=CC=CC=C21)C(=O)O

Technology Process of (S)-3-(Benzo[b]thiophen-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

There total 4 articles about (S)-3-(Benzo[b]thiophen-3-yl)-2-((tert-butoxycarbonyl)amino)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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-amino-3-<1>benzothiophene-3-ylpropionic acid (72120-71-9) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-(benzo[b]thiophen-3-yl)propanoic acid (154902-51-9)

Guidance literature:

With triethylamine; In water; acetone;

DOI:10.1021/jm00039a022

Reference yield:

3-chloromethylbenzothiophene (3216-47-5) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-(benzo[b]thiophen-3-yl)propanoic acid (154902-51-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / NaOEt / ethanol

2: 92.9 percent / KOH / H₂O

3: 39.3 percent / Acylase Amano 15000, NaOH, CoCl₂*6H₂O / H₂O / 37 °C / pH=7.5

4: 100 percent / Et₃N / acetone; H₂O

With potassium hydroxide; sodium hydroxide; Acylase Amano 15000; sodium ethanolate; triethylamine; cobalt(II) chloride; In ethanol; water; acetone;

DOI:10.1021/jm00039a022

Reference yield:

α-acetamido-β-<1>benzothiophene-3-ylpropionic acid (63024-19-1) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-(benzo[b]thiophen-3-yl)propanoic acid (154902-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 39.3 percent / Acylase Amano 15000, NaOH, CoCl₂*6H₂O / H₂O / 37 °C / pH=7.5

2: 100 percent / Et₃N / acetone; H₂O

With sodium hydroxide; Acylase Amano 15000; triethylamine; cobalt(II) chloride; In water; acetone;

DOI:10.1021/jm00039a022

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-amino-3-<1>benzothiophene-3-ylpropionic acid

3-chloromethylbenzothiophene

α-acetamido-β-<1>benzothiophene-3-ylpropionic acid

Downstream raw materials:

(2S,4R)-2-[(S)-2-Benzo[b]thiophen-3-yl-1-(benzyl-methyl-carbamoyl)-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

(R)-N¹-((S)-2-Benzo[b]thiophen-3-yl-1-methylcarbamoyl-ethyl)-N⁴-benzyloxy-2-isobutyl-succinamide

4-{(2S)-2-amino-3-[1-(2S)-2-benzo[b]thiophen-3-yl-1-benzylcarbamoylethylcarbamoyl-(2S)-2-biphenyl-4-yl-ethylcarbamoyl]-3(S)-sulfanylpropyl}benzoic acid

Refernces

• 1、 Hagiwara, Daijiro,Miyake, Hiroshi,Igari, Norihiro,Karino, Masako,Maeda, Yasue,et al.. "Studies of Neurokinin Antagonists. 4. Synthesis and Structure-Activity Relationships of Novel Dipeptide Substance P Antagonists: N2--L-prolyl>-N-methyl-N-(phenylmethyl)-3-(2-naphthyl)-L-alaninamide and Its Related Compounds". . p. 2090 - 2099. Retrieved 2007/10/02.