(R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acid

Base Information

• Chemical Name: (R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acid
• CAS No.: 159634-94-3
• Molecular Formula: C20H27N3O5
• Molecular Weight: 389.451
• Hs Code.: 2933990090
• Nikkaji Number: J3.204.776I
• Mol file: 159634-94-3.mol

Synonyms:159634-94-3;(R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acid;D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-;(2R)-3-(1H-indol-3-yl)-2-[[2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoic acid;(2R)-2-{2-[(tert-butoxy)carbonylamino]-2-methylpropanoylamino}-3-indol-3-ylpropanoic acid;d-tryptophan, n-[n-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl]-;anamorelin intermediate 4;(2R)-2-(2-[(tert-butoxy)carbonylamino]-2-methylpropanoylamino}-3-indol-3-ylpropanoic acid;(2R)-2-{2-[(tert-butoxy)carbonylamino]-2-methylpropanoylamino)-3-indol-3-ylpropanoic acid;(R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methyl-propanamido)-3-(1H-indol-3-yl)propanoic acid;DSCBSBPYDCIRPP-OAHLLOKOSA-N;N-[N-[(1,1-Dimethylethoxy)carbonyl]-2-methylalanyl]-D-tryptophan;SCHEMBL5253093;CS-M3097;MFCD08704784;AKOS015909338;AC-29225;CS-13159;(R)-2-(2-(tert-butoxycarbonylamino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acid;(R)-alpha-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid;alpha(R)-[[2-[[(1,1-dimethylethoxy)-carbonyl]amino]-2,2-dimethyl-1-oxoethyl]amino]-1H-indole-3propanoic acid;alpha(R)-[[2-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethyl-1-oxoethyl]amino]-1H-indole-3-propanoic acid

Chemical Property of (R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acid

Chemical Property:

• Boiling Point: 664.2±55.0 °C(Predicted)
• PKA: 3.49±0.10(Predicted)
• PSA: 120.52000
• Density: 1.243±0.06 g/cm3(Predicted)
• LogP: 3.36490
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 389.19507097
• Heavy Atom Count: 28
• Complexity: 599

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C)(C)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)NC(C)(C)C(=O)N[C@H](CC1=CNC2=CC=CC=C21)C(=O)O

Technology Process of (R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acid

There total 10 articles about (R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(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:

D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7) → (R)-2-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionic acid (159634-94-3)

Guidance literature:

With 4-methyl-morpholine; In 1,4-dioxane; water; ethyl acetate;

Reference yield:

(R)-α-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, benzyl ester (159634-93-2) → (R)-2-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionic acid (159634-94-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; under 760 Torr;

DOI:10.1016/S0960-894X(98)00103-6

Reference yield:

D-tryptophan benzyl ester (141595-98-4) → (R)-2-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionic acid (159634-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1: HOBt, EDC / Ambient temperature

2: H₂ / Pd/C

With hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal;

DOI:10.1016/S0960-894X(98)00238-8

upstream raw materials:

(R)-α-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, benzyl ester

Boc-D-Trp-OH

D-tryptophan benzyl ester

(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester

Downstream raw materials:

(R,R)-{1-[2-[3-benzyl-3-(N,N',N'-trimethyl-hydrazinocarbonyl)piperidin-1-yl]-1-(1H-indol-3-ylmethyl)-2-oxo-ethylcarbamoyl]-1-methylethyl}carbamic acid tert-butyl ester

(S,R)-{1-[2-[3-benzyl-3-(N,N',N'-trimethyl-hydrazinocarbonyl)piperidin-1-yl]-1-(1H-indol-3-ylmethyl)-2-oxo-ethylcarbamoyl]-1-methylethyl}carbamic acid tert-butyl ester

RC-1291 fumarate

Anamorelin

Refernces

• 1、 -. "Treatment of insulin resistance with growth hormone secretagogues". . . Retrieved 2008/06/13.
• 2、 -. "Dipeptides which promote release of growth hormone". . . Retrieved 2008/06/13.