(2R)-N-[(2S)-3,3-dimethyl-1-oxo-1-[[(1R)-1-phenylethyl]amino]butan-2-yl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide

Base Information

• Chemical Name: (2R)-N-[(2S)-3,3-dimethyl-1-oxo-1-[[(1R)-1-phenylethyl]amino]butan-2-yl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide
• CAS No.: 230961-08-7
• Molecular Formula: C34H43N3O4
• Molecular Weight: 557.72
• European Community (EC) Number: 687-112-9
• DSSTox Substance ID: DTXSID50438778
• Nikkaji Number: J1.508.745E
• Wikidata: Q27089078
• Pharos Ligand ID: DL9N2QSN7LVL
• ChEMBL ID: CHEMBL117225
• Mol file: 230961-08-7.mol

Synonyms:UK 356618;230961-08-7;UK-356618;(2R)-N-[(2S)-3,3-dimethyl-1-oxo-1-[[(1R)-1-phenylethyl]amino]butan-2-yl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide;CHEMBL117225;(R)-N1-((S)-3,3-dimethyl-1-oxo-1-((R)-1-phenylethylamino)butan-2-yl)-N4-hydroxy-2-(3-(2-methylbiphenyl-4-yl)propyl)succinamide;CID 10370504;UK-356,618;D0NP8A;GTPL6528;SCHEMBL6437730;CHEBI:94305;DTXSID50438778;JJHRUUKMPWUYIB-HVOSOHGQSA-N;BDBM50097263;AKOS024458021;(2R)-N1-[(1S)-2,2-Dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-2-{3-[(3-methyl-4-phenyl)-phenyl]propyl}-(N4-hydroxy)butanediamide;MS-30155;HY-107394;CS-0028365;PF 03890101;E98929;UK-356618, >=98% (HPLC);J-014983;BRD-K57011718-001-01-5;Q27089078;(R)-N*1*-[(S)-2,2-Dimethyl-1-((R)-1-phenyl-ethylcarbamoyl)-propyl]-N*4*-hydroxy-2-[3-(2-methyl-biphenyl-4-yl)-propyl]-succinamide;N*1*-[2,2-Dimethyl-1-(1-phenyl-ethylcarbamoyl)-propyl]-N*4*-hydroxy-2-[3-(2-methyl-biphenyl-4-yl)-propyl]-succinamide

Chemical Property of (2R)-N-[(2S)-3,3-dimethyl-1-oxo-1-[[(1R)-1-phenylethyl]amino]butan-2-yl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide

Chemical Property:

• PSA: 118.00000
• LogP: 8.42560
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: ≥25mg/mL
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 557.32535686
• Heavy Atom Count: 41
• Complexity: 828

Purity/Quality:

≥95% by HPLC ^*data from raw suppliers

UK-356618 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)CCCC(CC(=O)NO)C(=O)NC(C(=O)NC(C)C2=CC=CC=C2)C(C)(C)C)C3=CC=CC=C3
• Isomeric SMILES: CC1=C(C=CC(=C1)CCC[C@H](CC(=O)NO)C(=O)N[C@H](C(=O)N[C@H](C)C2=CC=CC=C2)C(C)(C)C)C3=CC=CC=C3
• Uses: Potent and selective inhibitor of matrix metalloprotease-3 (MMP-3) (IC50 = 5.9 nM). Displays selectivity over a range of MMPs (IC50 values are 73, 840, 1790, 1900 and 51000 for MMP-13, MMP-9, MMP-2, MMP-14 and MMP-1 respectively).

Technology Process of (2R)-N-[(2S)-3,3-dimethyl-1-oxo-1-[[(1R)-1-phenylethyl]amino]butan-2-yl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide

There total 14 articles about (2R)-N-[(2S)-3,3-dimethyl-1-oxo-1-[[(1R)-1-phenylethyl]amino]butan-2-yl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide 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: 59.0%

N1-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-(2R)-2-{3-[3-methyl-(4-phenyl)phenyl]propyl}-(N4-3-propenyloxy)butanediamide (230961-45-2) → UK-356618 (230961-08-7)

Guidance literature:

With ammonium formate; bis(triphenylphosphine) palladium (Il) acetate; In ethanol; water; for 1.5h; Heating / reflux;

Reference yield:

3-methyl-4-phenylbromobenzene (5002-26-6) → UK-356618 (230961-08-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 5 mol percent Pd(OAc)2*2P(o-tol)3; Et₃N / dimethylformamide / 100 °C

2: H₂ / 10 percent Pd/C / ethanol / 20 °C / 2250.18 Torr

3: HCl gas / CH₂Cl₂ / 0 °C

4: N-ethyl-N'-dimethylaminopropylcarbodiimide; 7-aza-1-hydroxy-1,2,3-benzotriazole; Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

5: ammonium formate / Pd(OAc)2*2PPh₃ / ethanol; H₂O / 2 h / Heating

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; Pd(OAc)2[P(2-tolyl)3]2; hydrogen; ammonium formate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; bis(triphenylphosphine) palladium (Il) acetate; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Heck reaction;

DOI:10.1016/S0960-894X(00)00720-4

Reference yield:

(R)-2-(2-(tert-butoxy)-2-oxoethyl)pent-4-enoic acid (179533-97-2) → UK-356618 (230961-08-7)

Guidance literature:

Multi-step reaction with 6 steps

1: N-ethyl-N'-dimethylaminopropylcarbodiimide; 7-aza-1-hydroxy-1,2,3-benzotriazole; N-methylmorpholine / CH₂Cl₂ / 18 h / 0 - 20 °C

2: 5 mol percent Pd(OAc)2*2P(o-tol)3; Et₃N / dimethylformamide / 100 °C

3: H₂ / 10 percent Pd/C / ethanol / 20 °C / 2250.18 Torr

4: HCl gas / CH₂Cl₂ / 0 °C

5: N-ethyl-N'-dimethylaminopropylcarbodiimide; 7-aza-1-hydroxy-1,2,3-benzotriazole; Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

6: ammonium formate / Pd(OAc)2*2PPh₃ / ethanol; H₂O / 2 h / Heating

With 4-methyl-morpholine; hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; Pd(OAc)2[P(2-tolyl)3]2; hydrogen; ammonium formate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; bis(triphenylphosphine) palladium (Il) acetate; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; 2: Heck reaction;

DOI:10.1016/S0960-894X(00)00720-4

upstream raw materials:

N₁-[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-(2R)-2-{3-[3-methyl-(4-phenyl)phenyl]propyl}-(N₄-3-propenyloxy)butanediamide

3-methyl-4-phenylbromobenzene

(R)-2-(2-(tert-butoxy)-2-oxoethyl)pent-4-enoic acid

tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)hex-5-enoate