Benzyl [4-(dimethylamino)-1-hydroxy-4-oxobutan-2-yl]carbamate

Base Information

• Chemical Name: Benzyl [4-(dimethylamino)-1-hydroxy-4-oxobutan-2-yl]carbamate
• CAS No.: 870812-29-6
• Molecular Formula: C14H20N2O4
• Molecular Weight: 280.324
• DSSTox Substance ID: DTXSID60700736
• Mol file: 870812-29-6.mol

Synonyms:DTXSID60700736;Carbamic acid, N-[(1R)-3-(dimethylamino)-1-(hydroxymethyl)-3-oxopropyl]-, phenylmethyl ester;MFCD16251359;SY291238;FT-0667387;(R)-3-(Cbz-amino)-4-hydroxy-N,N-dimethylbutanamide;Benzyl [4-(dimethylamino)-1-hydroxy-4-oxobutan-2-yl]carbamate

Chemical Property of Benzyl [4-(dimethylamino)-1-hydroxy-4-oxobutan-2-yl]carbamate

Chemical Property:

• PSA: 82.36000
• LogP: 0.95640
• Solubility.: Chloroform, DMSO, Methanol
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 280.14230712
• Heavy Atom Count: 20
• Complexity: 314

Purity/Quality:

95% ^*data from raw suppliers

N-[(1R)-3-(Dimethylamino)-1-(hydroxymethyl)-3-oxopropyl]carbamicAcidPhenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(=O)CC(CO)NC(=O)OCC1=CC=CC=C1
• Uses: N-[(1R)-3-(Dimethylamino)-1-(hydroxymethyl)-3-oxopropyl]carbamic Acid Phenylmethyl Ester can act as intermediate used in the preparation of N-sulfonylcarboximidamides to trigger cell death.

Technology Process of Benzyl [4-(dimethylamino)-1-hydroxy-4-oxobutan-2-yl]carbamate

There total 5 articles about Benzyl [4-(dimethylamino)-1-hydroxy-4-oxobutan-2-yl]carbamate 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: 99.0%

(R)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone (118399-28-3) + dimethyl amine (124-40-3) → benzyl (1R)-3-(dimethylamino)-1-(hydroxymethyl)-3-oxopropylcarbamate (870812-29-6)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 16h;

Reference yield:

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate (87219-29-2) + dimethyl amine (124-40-3) → benzyl (1R)-3-(dimethylamino)-1-(hydroxymethyl)-3-oxopropylcarbamate (870812-29-6)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 16h;

Reference yield:

benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate (75443-62-8) → benzyl (1R)-3-(dimethylamino)-1-(hydroxymethyl)-3-oxopropylcarbamate (870812-29-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 6 h / 0 - 25 °C

1.2: 0 °C / pH 4

2.1: toluene-4-sulfonic acid / toluene / 3 h / Dean-Stark conditions; Reflux

3.1: tetrahydrofuran / 14 h / 18 - 25 °C

With sodium tetrahydroborate; toluene-4-sulfonic acid; In tetrahydrofuran; toluene;

upstream raw materials:

(R)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone

dimethyl amine

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate

Downstream raw materials:

benzyl {(1R)-3-(dimethylamino)-3-oxo-1-[(phenylthio)methyl]propyl}carbamate

C₁₅H₂₂N₂O₆S

4-(((1R)-3-(dimethylamino)-1-((phenylthio)methyl)propyl)amino)-3-nitrobenzenesulfonamide

(3R)-3-amino-N,N-dimethyl-4-(phenylthio)butanamide

Refernces

• 1、 -. "APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES". Page/Page column 42. . Retrieved 2010/08/07.
• 2、 -. "N-sulfonylcarboximidamide apoptosis promoters". Page/Page column 11. . Retrieved 2008/06/13.