CARBAMIC ACID, N-[2-[(R)-(3-CHLOROPHENYL)[(3R)-1-[[[(2S)-2-(METHYLAMINO)-3-[(3R)-TETRAHYDRO-2H-PYRAN-3-YL]PROPYL]AMINO]CARBONYL]-3-PIPERIDINYL]METHOXY]ETHYL]-, METHYL ESTER, 2,2,2-TRIFLUOROACETATE (1:1)

Base Information

• Chemical Name: CARBAMIC ACID, N-[2-[(R)-(3-CHLOROPHENYL)[(3R)-1-[[[(2S)-2-(METHYLAMINO)-3-[(3R)-TETRAHYDRO-2H-PYRAN-3-YL]PROPYL]AMINO]CARBONYL]-3-PIPERIDINYL]METHOXY]ETHYL]-, METHYL ESTER, 2,2,2-TRIFLUOROACETATE (1:1)
• CAS No.: 1013937-63-7
• Molecular Formula: C26H41ClN4O5^.C2HF3O2
• Molecular Weight: 639.10
• Mol file: 1013937-63-7.mol

Synonyms:Carbamic acid, N-[2-[(R)-(3-chlorophenyl)[(3R)-1-[[[(2S)-2-(methylamino)-3-[(3R)-tetrahydro-2H-pyran-3-yl]propyl]amino]carbonyl]-3-piperidinyl]methoxy]ethyl]-, methyl ester, 2,2,2-trifluoroacetate (1:1);

Chemical Property of CARBAMIC ACID, N-[2-[(R)-(3-CHLOROPHENYL)[(3R)-1-[[[(2S)-2-(METHYLAMINO)-3-[(3R)-TETRAHYDRO-2H-PYRAN-3-YL]PROPYL]AMINO]CARBONYL]-3-PIPERIDINYL]METHOXY]ETHYL]-, METHYL ESTER, 2,2,2-TRIFLUOROACETATE (1:1)

Chemical Property:

• PSA: 138.46000
• LogP: 5.32390

Purity/Quality:

97% ^*data from raw suppliers

VTP 27999 Trifluoroacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: VTP 27999 Trifluoroacetate is a highly potent and selective renin inhibitor.

Technology Process of CARBAMIC ACID, N-[2-[(R)-(3-CHLOROPHENYL)[(3R)-1-[[[(2S)-2-(METHYLAMINO)-3-[(3R)-TETRAHYDRO-2H-PYRAN-3-YL]PROPYL]AMINO]CARBONYL]-3-PIPERIDINYL]METHOXY]ETHYL]-, METHYL ESTER, 2,2,2-TRIFLUOROACETATE (1:1)

There total 25 articles about CARBAMIC ACID, N-[2-[(R)-(3-CHLOROPHENYL)[(3R)-1-[[[(2S)-2-(METHYLAMINO)-3-[(3R)-TETRAHYDRO-2H-PYRAN-3-YL]PROPYL]AMINO]CARBONYL]-3-PIPERIDINYL]METHOXY]ETHYL]-, METHYL ESTER, 2,2,2-TRIFLUOROACETATE (1:1) 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: 54.0%

tert-butyl ((S)-1-((R)-3-((R)-(3-chlorophenyl)(2-((methoxycarbonyl)amino)ethoxy)methyl)piperidine-1-carboxamido)-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)(methyl)carbamate trifluoroacetate → methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate (1013937-63-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.5h;

DOI:10.1021/ml200137x

Reference yield:

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (942142-74-7) → methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate (1013937-63-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

1.2: 0 - 20 °C

2.1: sodium tetrahydroborate / methanol / 20 °C

3.1: triethylamine / dichloromethane / 3 h / -5 - 20 °C

4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C

5.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C

6.1: dmap; triethylamine / dichloromethane / 0 - 5 °C

7.1: dichloromethane / 1 h / 20 °C

8.1: triethylamine / dichloromethane

9.1: trifluoroacetic acid / dichloromethane / 0.5 h

With dmap; sodium tetrahydroborate; sodium azide; water; sodium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ml200137x

Reference yield:

(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (884510-86-5) → methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate (1013937-63-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: R-CBS-oxazaborolidine / tetrahydrofuran; toluene / -15 °C / Inert atmosphere

2.2: -15 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

3.2: 0 - 20 °C

4.1: sodium tetrahydroborate / methanol / 20 °C

5.1: triethylamine / dichloromethane / 3 h / -5 - 20 °C

6.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C

7.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C

8.1: dmap; triethylamine / dichloromethane / 0 - 5 °C

9.1: dichloromethane / 1 h / 20 °C

10.1: triethylamine / dichloromethane

11.1: trifluoroacetic acid / dichloromethane / 0.5 h

With dmap; sodium tetrahydroborate; n-butyllithium; sodium azide; water; sodium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1021/ml200137x

upstream raw materials:

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate

(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

(R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate

Downstream raw materials:

VTP-27999