2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester)

Base Information

• Chemical Name: 2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester)
• CAS No.: 170450-78-9
• Molecular Formula: C₂₃H₃₃NO₅
• Molecular Weight: 403.519
• Mol file: 170450-78-9.mol

Synonyms:2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester)

Chemical Property of 2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester)

There total 2 articles about 2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(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: 61.0%

(S)-4-benzyl-3-(4-methylpentanoyl)oxazolidin-2-one (113543-30-9) + (-)-(2S)-trifluoromethanesulfonyloxy-propionic acid tert-butyl ester (111757-80-3) → 2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester) (170450-78-9) + 2(S)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; Yields of byproduct given; 1.) -78 deg C, 30 min, 2.) -78 deg C, 2 h; -78 to r.t , 16 h;

DOI:10.1021/jo00120a022

Reference yield:

(+)-tert-butyl D-lactate (13650-70-9) → 2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester) (170450-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / tetrahydrofuran / -78 °C

2: KHMDS / tetrahydrofuran / -78 °C

With pyridine; potassium hexamethylsilazane; In tetrahydrofuran;

DOI:10.1021/jo00120a022

Reference yield:

2(R)-Isobutyl-3(S)-methylsuccinic acid 1-<4(S)-(phenylmethyl)-2-oxooxazolidinamide>-4-(tert-butyl ester) (170450-78-9) → KB-R7785 (168158-16-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / 30percent aq. H₂O₂, LiOH*H₂O / tetrahydrofuran / 1.) 0 deg C -5 deg C, 13 h, 2.) RT, 4 h

2: 42 percent / HOBT, 1-(3-(dimethylamino)propyl-3-ethylcarbodiimide / dimethylformamide; CH₂Cl₂ / Ambient temperature

3: HCOOH / 3 h / Ambient temperature

4: 57 percent / triethylamine, HOBT, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide / dimethylformamide; CH₂Cl₂ / 17 h / Ambient temperature

5: 85 percent / H₂ / 10percent Pd/C / methanol / Ambient temperature

With lithium hydroxide; formic acid; hydrogen; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00028-X

upstream raw materials:

(S)-4-benzyl-3-(4-methylpentanoyl)oxazolidin-2-one

(-)-(2S)-trifluoromethanesulfonyloxy-propionic acid tert-butyl ester

(+)-tert-butyl D-lactate

Downstream raw materials:

(2S,3R)-2,5-Dimethyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-hexanoic acid tert-butyl ester

(2S,3R)-2,5-Dimethyl-3-[((S)-methylcarbamoyl-phenyl-methyl)-carbamoyl]-hexanoic acid

KB-R₇₇₈₅

(2R,3S)-N⁴-Benzyloxy-2-isobutyl-3-methyl-N¹-((S)-methylcarbamoyl-phenyl-methyl)-succinamide