2-{(S)-3-[2-(2-Formyl-pyridin-3-yl)-ethyl]-2-oxo-oxazolidin-4-ylmethylene}-malonic acid di-tert-butyl ester

Base Information

• Chemical Name: 2-{(S)-3-[2-(2-Formyl-pyridin-3-yl)-ethyl]-2-oxo-oxazolidin-4-ylmethylene}-malonic acid di-tert-butyl ester
• CAS No.: 146885-92-9
• Molecular Formula: C₂₃H₃₀N₂O₇
• Molecular Weight: 446.5
• Mol file: 146885-92-9.mol

Synonyms:

Chemical Property of 2-{(S)-3-[2-(2-Formyl-pyridin-3-yl)-ethyl]-2-oxo-oxazolidin-4-ylmethylene}-malonic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(S)-3-[2-(2-Formyl-pyridin-3-yl)-ethyl]-2-oxo-oxazolidin-4-ylmethylene}-malonic acid di-tert-butyl ester

There total 13 articles about 2-{(S)-3-[2-(2-Formyl-pyridin-3-yl)-ethyl]-2-oxo-oxazolidin-4-ylmethylene}-malonic acid di-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:

3-pyridinylethanol (6293-56-7) → 2-{(S)-3-[2-(2-Formyl-pyridin-3-yl)-ethyl]-2-oxo-oxazolidin-4-ylmethylene}-malonic acid di-tert-butyl ester (146885-92-9)

Guidance literature:

Multi-step reaction with 11 steps

1: mCPBA

2: Me₂NCOCl / CH₂Cl₂

3: methanol

4: CH₂Cl₂

5: 70 percent / KH / CH₂Cl₂ / Ambient temperature

6: 1) BF₃ * MeOH, 2) NaBH₄ / 1) 120 deg C

7: imidazole

8: 1) O₃, 2) NaH / 1) methanol, -78 deg C, 2) CH₂Cl₂, -78 deg C

9: MsCl, Et₃N

10: CSA / ethanol

11: Dess-Martin periodinane (DMP)

With 1H-imidazole; sodium tetrahydroborate; camphor-10-sulfonic acid; boron trifluoride methanol complex; potassium hydride; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)60580-4

Reference yield:

methyl pyridine-3-acetate (39998-25-9) → 2-{(S)-3-[2-(2-Formyl-pyridin-3-yl)-ethyl]-2-oxo-oxazolidin-4-ylmethylene}-malonic acid di-tert-butyl ester (146885-92-9)

Guidance literature:

Multi-step reaction with 12 steps

1: LiAlH₄

2: mCPBA

3: Me₂NCOCl / CH₂Cl₂

4: methanol

5: CH₂Cl₂

6: 70 percent / KH / CH₂Cl₂ / Ambient temperature

7: 1) BF₃ * MeOH, 2) NaBH₄ / 1) 120 deg C

8: imidazole

9: 1) O₃, 2) NaH / 1) methanol, -78 deg C, 2) CH₂Cl₂, -78 deg C

10: MsCl, Et₃N

11: CSA / ethanol

12: Dess-Martin periodinane (DMP)

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; camphor-10-sulfonic acid; boron trifluoride methanol complex; potassium hydride; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)60580-4

Reference yield:

3-pyridineacetic acid hydrochloride (6419-36-9) → 2-{(S)-3-[2-(2-Formyl-pyridin-3-yl)-ethyl]-2-oxo-oxazolidin-4-ylmethylene}-malonic acid di-tert-butyl ester (146885-92-9)

Guidance literature:

Multi-step reaction with 13 steps

1: SOCl₂

2: LiAlH₄

3: mCPBA

4: Me₂NCOCl / CH₂Cl₂

5: methanol

6: CH₂Cl₂

7: 70 percent / KH / CH₂Cl₂ / Ambient temperature

8: 1) BF₃ * MeOH, 2) NaBH₄ / 1) 120 deg C

9: imidazole

10: 1) O₃, 2) NaH / 1) methanol, -78 deg C, 2) CH₂Cl₂, -78 deg C

11: MsCl, Et₃N

12: CSA / ethanol

13: Dess-Martin periodinane (DMP)

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; thionyl chloride; camphor-10-sulfonic acid; boron trifluoride methanol complex; potassium hydride; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)60580-4

upstream raw materials:

3-pyridinylethanol

methyl pyridine-3-acetate

3-pyridineacetic acid hydrochloride

2-(1-Oxy-pyridin-3-yl)-ethanol

Downstream raw materials:

acromelic acid E

acromelic acid B

Refernces