3-(S)-(4-(S)-ISOPROPYL-2-OXO-OXAZOLIDINE-3-CARBONYL)-OCTANOIC ACID TERT-BUTYL ESTER

Base Information

• Chemical Name: 3-(S)-(4-(S)-ISOPROPYL-2-OXO-OXAZOLIDINE-3-CARBONYL)-OCTANOIC ACID TERT-BUTYL ESTER
• CAS No.: 147961-55-5
• Molecular Formula: C₁₉H₃₃NO₅
• Molecular Weight: 355.475
• Mol file: 147961-55-5.mol

Synonyms:3-(S)-(4-(S)-ISOPROPYL-2-OXO-OXAZOLIDINE-3-CARBONYL)-OCTANOIC ACID TERT-BUTYL ESTER;[S-(R*,S*)]-4-(1-Methylethyl)-γ,2-dioxo-β-pentyl-3-oxazolidinebutanoic Acid 1,1-DiMethylethyl Ester

Chemical Property of 3-(S)-(4-(S)-ISOPROPYL-2-OXO-OXAZOLIDINE-3-CARBONYL)-OCTANOIC ACID TERT-BUTYL ESTER

Chemical Property:

• Boiling Point: 466.1±28.0 °C(Predicted)
• PKA: -2.43±0.40(Predicted)
• PSA: 72.91000
• Density: 1.057±0.06 g/cm3(Predicted)
• LogP: 3.85600
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

98% ^*data from raw suppliers

3-(S)-(4-(S)-Isopropyl-2-oxo-oxazolidine-3-carbonyl)-octanoicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-(S)-(4-(S)-Isopropyl-2-oxo-oxazolidine-3-carbonyl)-octanoic Acid tert-Butyl Ester (cas# 147961-55-5) is a compound useful in organic synthesis.

Technology Process of 3-(S)-(4-(S)-ISOPROPYL-2-OXO-OXAZOLIDINE-3-CARBONYL)-OCTANOIC ACID TERT-BUTYL ESTER

There total 1 articles about 3-(S)-(4-(S)-ISOPROPYL-2-OXO-OXAZOLIDINE-3-CARBONYL)-OCTANOIC ACID TERT-BUTYL 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:

bromoacetic acid tert-butyl ester (5292-43-3) + (4S)-4-isopropyl-3-(1-oxoheptyl)-2-oxazolidinone (145588-98-3) → (4S)-4-isopropyl-3-<(2R)-2-(tert-butyloxycarbonylmethyl)-1-oxoheptyl>-2-oxazolidinone (147961-55-5)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -78 deg C, 2.) THF, -78 deg C;

DOI:10.1016/S0040-4039(00)61652-0

Reference yield:

(4S)-4-isopropyl-3-<(2R)-2-(tert-butyloxycarbonylmethyl)-1-oxoheptyl>-2-oxazolidinone (147961-55-5) → tert-butyl (3S)-1-benzyloxycarbonyl-2-<(2R)-1-oxo-2-<(2,2,2-trichloroethoxycarbonyl)methyl>heptyl>hexahydropyridazine-3-carboxylate (147983-31-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 1.65M BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, hexane, 1 h

2: 838 mg / 4N HCl / dioxane / Ambient temperature

3: oxalyl chloride / benzene / 2 h / 60 °C

4: pyridine / tetrahydrofuran / 1.5 h / -15 °C

5: H₂ / 10percent Pd/C / methanol / 2 h / Ambient temperature

6: oxalyl chloride / benzene / 2 h / 50 °C

7: N-ethylmorpholine / tetrahydrofuran / 1.) -15 deg C to r.t., 2.) r.t., overnight

With N-ethylmorpholine;; pyridine; hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; benzene;

DOI:10.7164/antibiotics.47.1481

Reference yield:

(4S)-4-isopropyl-3-<(2R)-2-(tert-butyloxycarbonylmethyl)-1-oxoheptyl>-2-oxazolidinone (147961-55-5) → tert-butyl (3S)-1-benzyloxycarbonyl-2-<(2R)-2-benzyloxyaminocarbonylmethyl-1-oxoheptyl>hexahydropyridazine-3-carboxylate (147983-33-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) 1.65M BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, hexane, 1 h

2: 838 mg / 4N HCl / dioxane / Ambient temperature

3: oxalyl chloride / benzene / 2 h / 60 °C

4: pyridine / tetrahydrofuran / 1.5 h / -15 °C

5: H₂ / 10percent Pd/C / methanol / 2 h / Ambient temperature

6: oxalyl chloride / benzene / 2 h / 50 °C

7: N-ethylmorpholine / tetrahydrofuran / 1.) -15 deg C to r.t., 2.) r.t., overnight

8: 96 percent / Zn, 1M NH₄OAc / tetrahydrofuran; H₂O / 2.5 h / Ambient temperature

9: 98 percent / Et₃N, DEPC / tetrahydrofuran; dimethylformamide / 4.5 h / -15 °C

With N-ethylmorpholine;; pyridine; hydrogenchloride; n-butyllithium; oxalyl dichloride; ammonium acetate; hydrogen; triethylamine; diethyl dicarbonate; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; benzene;

DOI:10.7164/antibiotics.47.1481

upstream raw materials:

bromoacetic acid tert-butyl ester

(4S)-4-isopropyl-3-(1-oxoheptyl)-2-oxazolidinone

Downstream raw materials:

tert-butyl (3R)-3-benzyloxycarbonyloctanoate

2-(R)-(tert-butoxycarbonylmethyl)heptanoic acid

tert-butyl (3S)-1-benzyloxycarbonyl-2-<(3R)-3-carboxy-1-oxooctyl>hexahydropyridazine-3-carboxylate

(3S)-1-benzyloxycarbonyl-2-<(3R)-3-benzyloxyaminocarbonyl-1-oxooctyl>hexahydropyridazine-3-carboxylic acid

Refernces

• 1、 Tamaki,Ogita,Tanzawa,Sugimura. "Synthesis and determination of the absolute configuration of matlystatin B". . p. 683 - 686. Retrieved 2007/10/02.