ChemicalBook CAS DataBase List 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)

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) synthesis

13synthesis methods

Product 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 Number:1013937-63-7
Molecular formula:C28H42ClF3N4O7
Molecular Weight:639.11

884510-86-5 Synthesis

1-Piperidinecarboxylic acid, 3-[(MethoxyMethylaMino)carbonyl]-, 1,1-diMethylethyl ester, (3R)-

884510-86-5
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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)

1013937-63-7
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$27.00/1mg

Yield:-

Steps:

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

References:

Jia, Lanqi;Simpson, Robert D.;Yuan, Jing;Xu, Zhenrong;Zhao, Wei;Cacatian, Salvacion;Tice, Colin M.;Guo, Joan;Ishchenko, Alexey;Singh, Suresh B.;Wu, Zhongren;McKeever, Brian M.;Bukhtiyarov, Yuri;Johnson, Judith A.;Doe, Christopher P.;Harrison, Richard K.;McGeehan, Gerard M.;Dillard, Lawrence W.;Baldwin, John J.;Claremon, David A. [ACS Medicinal Chemistry Letters,2011,vol. 2,# 10,p. 747 - 751]

942142-74-7 Synthesis