(S)-2-benzyloxycarbonyl-amino-3-methylbutyric acid-(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester

Base Information

• Chemical Name: (S)-2-benzyloxycarbonyl-amino-3-methylbutyric acid-(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester
• CAS No.: 1025504-76-0
• Molecular Formula: C₃₂H₄₄N₂O₆
• Molecular Weight: 552.711
• Mol file: 1025504-76-0.mol

Synonyms:(S)-2-benzyloxycarbonyl-amino-3-methylbutyric acid-(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester

Chemical Property of (S)-2-benzyloxycarbonyl-amino-3-methylbutyric acid-(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester

Chemical Property:

• Boiling Point: 658.5±55.0 °C(Predicted)
• Density: 1.17±0.1 g/cm3(Predicted)

Purity/Quality:

95%-98% ^*data from raw suppliers

N-CarboxybenzylValbenazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-Carboxybenzyl Valbenazine is an intermediate in the synthesis of Valbenzine (V087000), a highly selective vesicular monoamine transporter 2 inhibitor that is used in the treatment of tardive dykinesia.

Technology Process of (S)-2-benzyloxycarbonyl-amino-3-methylbutyric acid-(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester

There total 3 articles about (S)-2-benzyloxycarbonyl-amino-3-methylbutyric acid-(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester 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: 100.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + (2R,3R,11bR)-dihydrotetrabenazine → (S)-2-benzyloxycarbonyl-amino-3-methylbutyric acid-(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester (1025504-76-0)

Guidance literature:

(2R,3R,11bR)-dihydrotetrabenazine; With dmap; In dichloromethane;

(S)-N-(benzyloxycarbonyl)valine; In dichloromethane; for 0.0833333h;

With dicyclohexyl-carbodiimide; In dichloromethane;

Reference yield:

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one (58-46-8,1381929-92-5) → (S)-2-benzyloxycarbonyl-amino-3-methylbutyric acid-(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester (1025504-76-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (1S)-10-camphorsulfonic acid / acetone / 24 h / 16 - 31 °C

1.2: pH 8

2.1: dimethylsulfide borane complex / tetrahydrofuran / 2.5 h / -20 °C

3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane

With dmap; dimethylsulfide borane complex; (1S)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetone;

Reference yield:

((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one) (1026016-83-0,1381929-92-5) → (S)-2-benzyloxycarbonyl-amino-3-methylbutyric acid-(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester (1025504-76-0)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylsulfide borane complex / tetrahydrofuran / 2.5 h / -20 °C

2: dmap; dicyclohexyl-carbodiimide / dichloromethane

With dmap; dimethylsulfide borane complex; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

(3R^*,11bR^*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one)

Downstream raw materials:

(S)-2-amino-3-methylbutyric acid (2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolizin-2-yl ester

Refernces

• 1、 -. "SUBSTITUTED 3-ISOBUTYL-9, 10-DIMETHOXY-1,3,4,6,7,11B-HEXAHYDRO-2H-PYRIDO[2,1-A] ISOQUINOLIN-2-OL COMPOUNDS AND METHODS RELATING THERETO". Page/Page column 14-15. . Retrieved 2008/12/05.