{1-[2-(4-Carbamimidoyl-benzoylamino)-propionyl]-piperidin-4-yloxy}-acetic acid

Base Information

• Chemical Name: {1-[2-(4-Carbamimidoyl-benzoylamino)-propionyl]-piperidin-4-yloxy}-acetic acid
• CAS No.: 144412-18-0
• Molecular Formula: C18H24 N4 O5
• Molecular Weight: 376.412
• UNII: F23PXB8U2L
• DSSTox Substance ID: DTXSID101029735
• Nikkaji Number: J525.974F
• Wikipedia: Ro-44-3888
• Wikidata: Q7339192
• ChEMBL ID: CHEMBL65267
• Mol file: 144412-18-0.mol

Synonyms:((1-(2-((4-(aminoiminomethyl)benzoyl)amino)-1-oxopropyl)-4-piperidinyl)oxy)acetic acid;Ro 44-3888;Ro-44-3888

Chemical Property of {1-[2-(4-Carbamimidoyl-benzoylamino)-propionyl]-piperidin-4-yloxy}-acetic acid

Chemical Property:

• XLogP3: 0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 376.17466988
• Heavy Atom Count: 27
• Complexity: 566

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)N1CCC(CC1)OCC(=O)O)NC(=O)C2=CC=C(C=C2)C(=N)N
• Isomeric SMILES: C[C@@H](C(=O)N1CCC(CC1)OCC(=O)O)NC(=O)C2=CC=C(C=C2)C(=N)N

Technology Process of {1-[2-(4-Carbamimidoyl-benzoylamino)-propionyl]-piperidin-4-yloxy}-acetic acid

There total 9 articles about {1-[2-(4-Carbamimidoyl-benzoylamino)-propionyl]-piperidin-4-yloxy}-acetic 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:

4-HYDROXYPIPERIDINE (5382-16-1) → Ro 44-3888 (144412-18-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 63 percent / triethylamine (TEA) / CH₂Cl₂ / 16 h / Ambient temperature

2: 76 percent / tetra-n-butylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂; H₂O / 16 h

3: 94 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 760 Torr

4: 1.)2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT), N-methylmorpholine (NMM), 2.) N-methylmorpholine (NMM) / 1.) CH₂Cl₂, 0 deg C, 3 h, 2.) CH₂Cl₂, RT, 12 h

5: H₂ / 10percent Pd/C / ethanol; acetic acid / 3 h / 760 Torr

6: tetra-n-butylammonium hydrogen sulfate, aq. NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

7: trifluoroacetic acid (TFA) / CH₂Cl₂ / 2 h / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; water; acetic acid;

DOI:10.1021/jm00101a017

Reference yield:

1-(benzyloxycarbonyl)-4-hydroxypiperidine (95798-23-5) → Ro 44-3888 (144412-18-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / tetra-n-butylammonium hydrogen sulfate, aq. NaOH / CH₂Cl₂; H₂O / 16 h

2: 94 percent / H₂ / 10percent Pd/C / ethanol / 3 h / 760 Torr

3: 1.)2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT), N-methylmorpholine (NMM), 2.) N-methylmorpholine (NMM) / 1.) CH₂Cl₂, 0 deg C, 3 h, 2.) CH₂Cl₂, RT, 12 h

4: H₂ / 10percent Pd/C / ethanol; acetic acid / 3 h / 760 Torr

5: tetra-n-butylammonium hydrogen sulfate, aq. NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

6: trifluoroacetic acid (TFA) / CH₂Cl₂ / 2 h / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; water; acetic acid;

DOI:10.1021/jm00101a017

Reference yield:

(Piperidin-4-yloxy)-acetic acid tert-butyl ester (144412-03-3) → Ro 44-3888 (144412-18-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.)2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT), N-methylmorpholine (NMM), 2.) N-methylmorpholine (NMM) / 1.) CH₂Cl₂, 0 deg C, 3 h, 2.) CH₂Cl₂, RT, 12 h

2: H₂ / 10percent Pd/C / ethanol; acetic acid / 3 h / 760 Torr

3: tetra-n-butylammonium hydrogen sulfate, aq. NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

4: trifluoroacetic acid (TFA) / CH₂Cl₂ / 2 h / Ambient temperature

With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; acetic acid;

DOI:10.1021/jm00101a017

upstream raw materials:

{1-[(S)-2-(4-Carbamimidoyl-benzoylamino)-propionyl]-piperidin-4-yloxy}-acetic acid tert-butyl ester

4-HYDROXYPIPERIDINE

1-(benzyloxycarbonyl)-4-hydroxypiperidine

4-(aminoiminomethyl)benzoic acid