1(2H)-Pyridazinecarboxylic acid, tetrahydro-3-[[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]carbonyl]-, phenylmethyl ester, (3S)-

Base Information

• Chemical Name: 1(2H)-Pyridazinecarboxylic acid, tetrahydro-3-[[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]carbonyl]-, phenylmethyl ester, (3S)-
• CAS No.: 672307-41-4
• Molecular Formula: C23H25N3O5
• Molecular Weight: 423.469
• Mol file: 672307-41-4.mol

Synonyms:

Chemical Property of 1(2H)-Pyridazinecarboxylic acid, tetrahydro-3-[[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]carbonyl]-, phenylmethyl ester, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1(2H)-Pyridazinecarboxylic acid, tetrahydro-3-[[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]carbonyl]-, phenylmethyl ester, (3S)-

There total 5 articles about 1(2H)-Pyridazinecarboxylic acid, tetrahydro-3-[[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]carbonyl]-, phenylmethyl ester, (3S)- 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: 69.0%

benzyl chloroformate (501-53-1,94274-21-2) + (4S)-3-[[(3S)-hexahydro-3-pyridazinyl]carbonyl]-4-(phenylmethyl)-2-oxazolidinone dihydrochloride → phenylmethyl (3S)-hexahydro-3-[[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]carbonyl]-1-pyridazinecarboxylate (672307-41-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1021/jo035667t

Reference yield:

5-bromovaleroyl chloride (4509-90-4) → phenylmethyl (3S)-hexahydro-3-[[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]carbonyl]-1-pyridazinecarboxylate (672307-41-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / nBuLi / tetrahydrofuran / -78 °C

2: 99 percent / LDA; DMPU / -78 °C

3: HCl / dioxane; H₂O / 18 h / 20 °C

4: 69 percent / iPr₂NEt / dimethylformamide / 18 h / 20 °C

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo035667t

Reference yield:

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) → phenylmethyl (3S)-hexahydro-3-[[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]carbonyl]-1-pyridazinecarboxylate (672307-41-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / nBuLi / tetrahydrofuran / -78 °C

2: 99 percent / LDA; DMPU / -78 °C

3: HCl / dioxane; H₂O / 18 h / 20 °C

4: 69 percent / iPr₂NEt / dimethylformamide / 18 h / 20 °C

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo035667t

upstream raw materials:

benzyl chloroformate

5-bromovaleroyl chloride

(S)-4-Benzyl-2-oxazolidinone

(S)-4-benzyl-3-(5-bromopentanoyl)oxazolidine-2-one

Downstream raw materials:

(S)-2-((R)-2-tert-Butoxycarbonylmethyl-5-methyl-hexanoyl)-3-((S)-1-isopropyl-2-oxo-butylcarbamoyl)-tetrahydro-pyridazine-1-carboxylic acid benzyl ester

(S)-2-((R)-2-Carboxymethyl-5-methyl-hexanoyl)-3-((S)-1-isopropyl-2-oxo-butylcarbamoyl)-tetrahydro-pyridazine-1-carboxylic acid benzyl ester

1-(phenylmethyl) hydrogen (3S)-2-[(2R)-2-[2-(1,1-dimethylethoxy)-2-oxoethyl]-5-methyl-1-oxohexyl]hexahydro-1,3-pyridazinedicarboxylate

(3S)-hexahydro-1,3-pridazinedicarboxylic acid 1-(phenylmethyl) ester