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

Base Information

• Chemical Name: 4-[[(1R)-2-[[(2R)-2-(2-adamantyloxycarbonylamino)-3-(1H-indol-3-yl)-2-methylpropanoyl]amino]-1-phenylethyl]amino]-4-oxobutanoic acid
• CAS No.: 130332-27-3
• Molecular Formula: C35H42N4O6
• Molecular Weight: 614.742
• UNII: 2637PDX9SI
• DSSTox Substance ID: DTXSID701099873
• Nikkaji Number: J360.238I
• Wikipedia: CI-988
• Wikidata: Q76009969
• Pharos Ligand ID: UB3APZZPPH7V,UB3XXNJFQJ9J
• ChEMBL ID: CHEMBL2062154,CHEMBL287735
• Mol file: 130332-27-3.mol

Synonyms:4-((2-((3-(1H-indol-3-yl)-2-methyl-1-oxo-2-(((tricyclo(3.3.1.1)-dec-2-yloxy)carbonyl)amino)propyl)amino)-1-phenethyl)amino)-4-oxobutanoate N-methyl-D-glucamine;CI 988;CI-988;PD 134308;PD-134308;PD134308

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 949.6°Cat760mmHg
• Flash Point: 528.1°C
• PSA: 149.62000
• Density: 1.32g/cm³
• LogP: 6.03120
• Storage Temp.: Store at +4°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 614.31043507
• Heavy Atom Count: 45
• Complexity: 1070

Purity/Quality:

99% ^*data from raw suppliers

CI-988 ^*data from reagent 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)CCC(=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)CCC(=O)O)NC(=O)OC4C5CC6CC(C5)CC4C6
• Uses: CI-988 is a potent and selective cholecystokinin 2 (CCK-2) receptor antagonist that displays ~ 1600-fold selectivity over CCK1 receptors and has negligible affinity at other binding sites. CI-988 exhibits anxiolytic activity following oral administration. CI-98 inhibited the proliferation of small cell lung cancer (SCLC) cells in mice.

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

There total 11 articles about 4-[[(1R)-2-[[(2R)-2-(2-adamantyloxycarbonylamino)-3-(1H-indol-3-yl)-2-methylpropanoyl]amino]-1-phenylethyl]amino]-4-oxobutanoic 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: 80.0%

succinic acid anhydride (108-30-5) + tricyclo<3.3.1.13,7>dec-2-yl *,R*)>-<2-<(2-amino-2-phenylethyl)amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>carbamate (130406-64-3) → N-{(R)-2-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-1-phenyl-ethyl}-succinamic acid (130332-27-3)

Guidance literature:

In ethyl acetate; for 24h; Ambient temperature;

DOI:10.1021/jm00105a062

Reference yield:

1-adamantanol (700-57-2) → N-{(R)-2-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-1-phenyl-ethyl}-succinamic acid (130332-27-3)

Guidance literature:

Multi-step reaction with 6 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: 80 percent / ethyl acetate / 24 h / Ambient temperature

With pyridine; lithium hydroxide; hydrogen; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/jm00105a062

Reference yield:

D-2-phenylglycinol (56613-80-0) → N-{(R)-2-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-1-phenyl-ethyl}-succinamic acid (130332-27-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / Et₃N / tetrahydrofuran / 18 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 18 h / Ambient temperature

3: NaN₃ / dimethylformamide / 3 h / 80 °C

4: Lindlar catalyst, H₂ / ethyl acetate / 6 h / 30 °C / 2327.2 Torr

5: 1.) 1-hydroxybenzotriazole hydrate, N,N'-dicyclohexylcarbodiimide / 1.) EtOAc, RT, 2 h, 2.) 18 h

6: 89 percent / H₂ / Pearlman's catalyst / ethanol / 18 h / 25 °C / 2327.2 Torr

7: 80 percent / ethyl acetate / 24 h / Ambient temperature

With Lindlar's catalyst; sodium azide; hydrogen; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00105a062

upstream raw materials:

succinic acid anhydride

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

1-adamantanol

D-2-phenylglycinol

Downstream raw materials:

-3-(1H-indol-3-ylmethyl)-3-methyl-4,9,12-trioxo-7-phenyl-14-oxa-2,5,8,13-tetraazapentadecanoic acid tricyclo<3.3.1.1^3,7>dec-2-yl ester

Refernces