Carbamic acid, N-[(1R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-, phenylmethyl ester

Base Information

• Chemical Name: Carbamic acid, N-[(1R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-, phenylmethyl ester
• CAS No.: 61535-47-5
• Molecular Formula: C19H20N2O3
• Molecular Weight: 324.379
• DSSTox Substance ID: DTXSID601157000
• Mol file: 61535-47-5.mol

Synonyms:61535-47-5;Carbamic acid, N-[(1R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-, phenylmethyl ester;SCHEMBL12113038;DTXSID601157000;Benzyl (R)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate;benzyl N-[(2R)-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl]carbamate;Phenylmethyl N-[(1R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]carbamate

Chemical Property of Carbamic acid, N-[(1R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-, phenylmethyl ester

Chemical Property:

• PSA: 74.35000
• LogP: 3.38860
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 324.14739250
• Heavy Atom Count: 24
• Complexity: 398

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CC2=CNC3=CC=CC=C32)CO
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@H](CC2=CNC3=CC=CC=C32)CO

Technology Process of Carbamic acid, N-[(1R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-, phenylmethyl ester

There total 10 articles about Carbamic acid, N-[(1R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-, phenylmethyl 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: 100.0%

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester (2717-76-2,130812-44-1,130812-46-3) → benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate (61535-47-5,58889-48-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; for 0.5h;

DOI:10.1039/c2cc31735d

Reference yield: 50.0%

(2R)-2-amino-3-(1H-indol-3-yl)propan-1-ol (154-09-6,526-53-4,2899-29-8,52485-52-6) + benzyl chloroformate (501-53-1,94274-21-2) → N-Cbz-D-tryptophanol (61535-47-5) + C22H24N2O3 (1193314-87-2)

Guidance literature:

With sodium carbonate; In acetone; at 20 ℃; Cooling with ice;

Reference yield: 50.0%

(2R)-2-amino-3-(1H-indol-3-yl)propan-1-ol (154-09-6,526-53-4,2899-29-8,52485-52-6) + benzyl chloroformate (501-53-1,94274-21-2) → N-Cbz-D-tryptophanol (61535-47-5)

Guidance literature:

With sodium carbonate; In water; acetone; at 0 - 20 ℃;

DOI:10.1021/jm100410f

upstream raw materials:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester

benzyl chloroformate

L-tryptophanol

(S)-tryptophan methyl ester hydrochloride

Downstream raw materials:

(S)-benzyl (1-(indol-3-yl)-3-oxopropan-2-yl)carbamate

(S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester

L-tryptophanol

Cyclohexanecarboxylic acid [(S)-1-hydroxymethyl-2-(1H-indol-3-yl)-ethyl]-amide