(E)-4-[[(1R)-2-[[(2R)-2-(2-adamantyloxycarbonylamino)-3-(1H-indol-3-yl)-2-methylpropanoyl]amino]-1-phenylethyl]amino]-4-oxobut-2-enoic acid

Base Information

Chemical Name:(E)-4-[[(1R)-2-[[(2R)-2-(2-adamantyloxycarbonylamino)-3-(1H-indol-3-yl)-2-methylpropanoyl]amino]-1-phenylethyl]amino]-4-oxobut-2-enoic acid
CAS No.:139067-52-0
Molecular Formula:C₃₅H₄₀N₄O₆
Molecular Weight:612.726
Hs Code.:
Nikkaji Number:J363.533C,J486.125F
Wikidata:Q27088262
Pharos Ligand ID:UBBA52XXUZYB
ChEMBL ID:CHEMBL341460,CHEMBL3351022

Synonyms:4-((2- ((3-(1H-indol-3-yl)-2-methyl-1-oxo-2-(((tricyclo(3.3.1.1(3,7))dec-2-yloxy)carbonyl)amino)propyl)amino)-1-phenylethyl)amino)-4-oxo-2-butenoic acid;CAM 1189;CAM-1189;CAM1189;PD 136450;PD-136450;PD136450

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-4-[[(1R)-2-[[(2R)-2-(2-adamantyloxycarbonylamino)-3-(1H-indol-3-yl)-2-methylpropanoyl]amino]-1-phenylethyl]amino]-4-oxobut-2-enoic acid

Chemical Property:

Vapor Pressure:0mmHg at 25°C
Boiling Point:950.4°Cat760mmHg
Flash Point:528.6°C
Density:1.33g/cm³
XLogP3:4.6
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:12
Exact Mass:612.29478501
Heavy Atom Count:45
Complexity:1110

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(CC1=CNC2=CC=CC=C21)(C(=O)NCC(C3=CC=CC=C3)NC(=O)C=CC(=O)O)NC(=O)OC4C5CC6CC(C5)CC4C6
Isomeric SMILES:C[C@@](CC1=CNC2=CC=CC=C21)(C(=O)NC[C@@H](C3=CC=CC=C3)NC(=O)/C=C/C(=O)O)NC(=O)OC4C5CC6CC(C5)CC4C6

Technology Process of (E)-4-[[(1R)-2-[[(2R)-2-(2-adamantyloxycarbonylamino)-3-(1H-indol-3-yl)-2-methylpropanoyl]amino]-1-phenylethyl]amino]-4-oxobut-2-enoic acid

There total 13 articles about (E)-4-[[(1R)-2-[[(2R)-2-(2-adamantyloxycarbonylamino)-3-(1H-indol-3-yl)-2-methylpropanoyl]amino]-1-phenylethyl]amino]-4-oxobut-2-enoic 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: 69.0%

: 108-31-6
maleic anhydride

: 130406-64-3
tricyclo<3.3.1.1^3,7>dec-2-yl *,R^*)>-<2-<(2-amino-2-phenylethyl)amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>carbamate

: 139067-52-0
-4-<<2-<<3-(1H-indol-3-yl)-2-methyl-1-oxo-2-<<(tricyclo<3.3.1.1^3,7>dec-2-yloxy)carbonyl>amino>propyl>amino>-1-phenylethyl>amino>-4-oxo-2-butenoic acid

Guidance literature:: In ethyl acetate; for 4h; Heating;
DOI:10.1016/0223-5234(93)90078-S

Reference yield: 46.0%

: 130406-65-4
tricyclo<3.3.1.1^3,7>dec-2-yl *,R^*)>-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,12-trioxo-7-phenyl-13-oxa-2,5,8-triazatetradec-10-enoate

: 130406-67-6,139067-52-0
PD 136450

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; at 0 ℃; for 4.5h;
DOI:10.1021/jm00105a062

Reference yield:

: 700-57-2
1-adamantanol

: 130406-67-6,139067-52-0
PD 136450

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 89 percent / Et₃N / tetrahydrofuran / 0.25 h

3: 90 percent / LiOH / H₂O; dioxane / 18 h / Ambient temperature

4: 1.) 1-hydroxybenzotriazole hydrate, N,N'-dicyclohexylcarbodiimide / 1.) EtOAc, RT, 2 h, 2.) 18 h

5: 89 percent / H₂ / Pearlman's catalyst / ethanol / 18 h / 25 °C / 2327.2 Torr

6: 1.) 1-hydroxybenzotriazole hydrate, N,N'-dicyclohexylcarbodiimide / 1.) EtOAc, 2 h, 2.) RT, 18 h

7: 46 percent / 0.1 M aq. LiOH / tetrahydrofuran / 4.5 h / 0 °C

With pyridine; lithium hydroxide; hydrogen; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water;
DOI:10.1021/jm00105a062