(2S,3S)-2-((S)-1-Benzoyloxy-2-methyl-propyl)-3-hydroxy-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S)-2-((S)-1-Benzoyloxy-2-methyl-propyl)-3-hydroxy-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 512184-27-9
• Molecular Formula: C₁₉H₂₅NO₆
• Molecular Weight: 363.411
• Mol file: 512184-27-9.mol

Synonyms:(2S,3S)-2-((S)-1-Benzoyloxy-2-methyl-propyl)-3-hydroxy-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property of (2S,3S)-2-((S)-1-Benzoyloxy-2-methyl-propyl)-3-hydroxy-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-((S)-1-Benzoyloxy-2-methyl-propyl)-3-hydroxy-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

There total 12 articles about (2S,3S)-2-((S)-1-Benzoyloxy-2-methyl-propyl)-3-hydroxy-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl 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: 89.0%

(4S,5S)-4-((S)-2-Ethoxycarbonyl-1-hydroxy-2-methyl-propyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (512184-26-8) → (2S,3S)-2-((S)-1-Benzoyloxy-2-methyl-propyl)-3-hydroxy-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (512184-27-9)

Guidance literature:

With hydrogenchloride; In methanol; for 5h; Heating;

DOI:10.1021/jo0268916

Reference yield:

methyl (2E)-4-methylpent-2-enoate (20515-15-5) → (2S,3S)-2-((S)-1-Benzoyloxy-2-methyl-propyl)-3-hydroxy-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (512184-27-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 92 percent / (DHQ)2PHAL; K₂OsO₂(OH)4; K₃[Fe(CN)6] / K₂CO₃; NaHCO₃ / 2-methyl-propan-2-ol; H₂O; various solvent(s) / 72 h / 5 °C

2.1: 100 percent / SOCl₂; pyridine / CH₂Cl₂ / cooling

3.1: 97 percent / NaIO₄; RuCl₃ / CCl₄; acetonitrile; H₂O / 1.5 h / 20 °C

4.1: 90 percent / NaN₃ / acetone; H₂O / 2 h / 20 °C

5.1: 99 percent / H₂ / Pd/C / ethanol; ethyl acetate / 24 h / 20 °C / 760 Torr

6.1: 85 percent / p-TsOH*H₂O / 1,2-dimethoxy-ethane / 4 h / Heating

7.1: 96 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 12 h / 20 °C

8.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

8.2: 81 percent / tetrahydrofuran; diethyl ether / 3 h / -78 °C

9.1: 99 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

10.1: 67 percent / LiClO₄ / CH₂Cl₂ / 5 h / 0 °C

11.1: 89 percent / aq. HCl / methanol / 5 h / Heating

With pyridine; hydrogenchloride; ruthenium trichloride; sodium periodate; thionyl chloride; sodium azide; Hydroquinone 1,4-phthalazinediyl diether; oxalyl dichloride; potassium dioxotetrahydroxoosmate(VI); hydrogen; lithium perchlorate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; potassium hexacyanoferrate(III); palladium on activated charcoal; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; water; ethyl acetate; acetone; acetonitrile; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 9.1: Swern oxidation / 10.1: Mukaiyama aldol coupling;

DOI:10.1021/jo0268916

Reference yield:

(2R,3S)-2,3-dihydroxy-4-methylpentanoic acid methyl ester (220805-65-2) → (2S,3S)-2-((S)-1-Benzoyloxy-2-methyl-propyl)-3-hydroxy-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (512184-27-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 100 percent / SOCl₂; pyridine / CH₂Cl₂ / cooling

2.1: 97 percent / NaIO₄; RuCl₃ / CCl₄; acetonitrile; H₂O / 1.5 h / 20 °C

3.1: 90 percent / NaN₃ / acetone; H₂O / 2 h / 20 °C

4.1: 99 percent / H₂ / Pd/C / ethanol; ethyl acetate / 24 h / 20 °C / 760 Torr

5.1: 85 percent / p-TsOH*H₂O / 1,2-dimethoxy-ethane / 4 h / Heating

6.1: 96 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 12 h / 20 °C

7.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

7.2: 81 percent / tetrahydrofuran; diethyl ether / 3 h / -78 °C

8.1: 99 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

9.1: 67 percent / LiClO₄ / CH₂Cl₂ / 5 h / 0 °C

10.1: 89 percent / aq. HCl / methanol / 5 h / Heating

With pyridine; hydrogenchloride; ruthenium trichloride; sodium periodate; thionyl chloride; sodium azide; oxalyl dichloride; hydrogen; lithium perchlorate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; ethanol; dichloromethane; water; ethyl acetate; acetone; acetonitrile; 8.1: Swern oxidation / 9.1: Mukaiyama aldol coupling;

DOI:10.1021/jo0268916

upstream raw materials:

(4S,5S)-4-((S)-2-Ethoxycarbonyl-1-hydroxy-2-methyl-propyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

methyl (2E)-4-methylpent-2-enoate

(2S,3S)-3-hydroxyleucine methyl ester

(4R,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

Downstream raw materials:

α-methylomuralide