Carbamic acid, N-((1R)-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-(((1S)-1-phenylethyl)amino)ethyl)-, 2-benzofuranylmethyl ester

Base Information

• Chemical Name: Carbamic acid, N-((1R)-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-(((1S)-1-phenylethyl)amino)ethyl)-, 2-benzofuranylmethyl ester
• CAS No.: 158991-23-2
• Molecular Formula: C30H29 N3 O4
• Molecular Weight: 495.578
• UNII: QK6IAJLA0M
• DSSTox Substance ID: DTXSID201107758
• Nikkaji Number: J652.749C
• Pharos Ligand ID: XLQNSKBW6ZCK
• ChEMBL ID: CHEMBL307488
• Mol file: 158991-23-2.mol

Synonyms:((2-benzofuran)-CH2OCO)-(R)-alpha-MeTrp-(S)-NHCH(CH3)Ph;2-benzofuranylmethoxycarbonyl-alpha-methyltryptophan-N-(1-phenylethyl)amide;PD 154075;PD-154075;(1-(1H-indol-3-ylmethyl)-1-methyl-2--oxo-2-((1-phenylethyl)amino)ethtyl)carbamic acid 2-benzofuranylmethyl ester;CI 1021;CI-1021;CI1021

Chemical Property of Carbamic acid, N-((1R)-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-(((1S)-1-phenylethyl)amino)ethyl)-, 2-benzofuranylmethyl ester

Chemical Property:

• XLogP3: 5.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 495.21580641
• Heavy Atom Count: 37
• Complexity: 787

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)NC(=O)C(C)(CC2=CNC3=CC=CC=C32)NC(=O)OCC4=CC5=CC=CC=C5O4
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)NC(=O)[C@@](C)(CC2=CNC3=CC=CC=C32)NC(=O)OCC4=CC5=CC=CC=C5O4

Technology Process of Carbamic acid, N-((1R)-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-(((1S)-1-phenylethyl)amino)ethyl)-, 2-benzofuranylmethyl ester

There total 3 articles about Carbamic acid, N-((1R)-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-(((1S)-1-phenylethyl)amino)ethyl)-, 2-benzofuranylmethyl ester 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: 74.0%

(S)-1-phenyl-ethylamine (2627-86-3) + (R)-N-[(benzo[b]furan-2-yl-methoxy)carbonyl]-2-methyltryptophan → PD 154075 (158991-23-2)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 30h;

DOI:10.1002/1099-1344(20001015)43:11<1087::AID-JLCR394>3.0.CO;2-7

Reference yield:

(E)-acetophenone O-methyloxime (15754-20-8) → PD 154075 (158991-23-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1S,2R-1-aminoindan-2-ol; BH₃-THF / tetrahydrofuran / -20 - 70 °C

2: 74 percent / HOBt; EDC; NMM / dimethylformamide / 30 h / 20 °C

With 4-methyl-morpholine; borane-THF; (1S,2R)-1-amino-2-indanol; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Reduction / 2: Acylation;

DOI:10.1002/1099-1344(20001015)43:11<1087::AID-JLCR394>3.0.CO;2-7

Reference yield:

acetophenone (98-86-2) → PD 154075 (158991-23-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / pyridine; MgSO₄ / ethanol / 20 h / 20 °C

2: 1S,2R-1-aminoindan-2-ol; BH₃-THF / tetrahydrofuran / -20 - 70 °C

3: 74 percent / HOBt; EDC; NMM / dimethylformamide / 30 h / 20 °C

With 4-methyl-morpholine; pyridine; borane-THF; magnesium sulfate; (1S,2R)-1-amino-2-indanol; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 1: Condensation / 2: Reduction / 3: Acylation;

DOI:10.1002/1099-1344(20001015)43:11<1087::AID-JLCR394>3.0.CO;2-7

upstream raw materials:

(S)-1-phenyl-ethylamine

(E)-acetophenone O-methyloxime

acetophenone

Downstream raw materials:

3-[(R)-2-(Benzofuran-2-ylmethoxycarbonylamino)-2-((S)-1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-(bis-benzyloxy-phosphoryloxymethyl)-benzoyloxymethyl ester

[(R)-2-{1-[2-(Bis-benzyloxy-phosphoryloxymethyl)-benzoyl]-1H-indol-3-yl}-1-methyl-1-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-carbamic acid benzofuran-2-ylmethyl ester

3-[(R)-2-(Benzofuran-2-ylmethoxycarbonylamino)-2-((S)-1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid bis-benzyloxy-phosphoryloxymethyl ester

[(R)-2-[1-(2-Iodomethyl-benzoyl)-1H-indol-3-yl]-1-methyl-1-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-carbamic acid benzofuran-2-ylmethyl ester

Refernces