(4S,5S)-4-Cyclohexylmethyl-5-{(S)-2-[(3-dimethylamino-propyl)-methyl-carbamoyl]-3-methyl-butyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S,5S)-4-Cyclohexylmethyl-5-{(S)-2-[(3-dimethylamino-propyl)-methyl-carbamoyl]-3-methyl-butyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 140660-89-5
• Molecular Formula: C₂₉H₅₅N₃O₄
• Molecular Weight: 509.773
• Mol file: 140660-89-5.mol

Synonyms:

Chemical Property of (4S,5S)-4-Cyclohexylmethyl-5-{(S)-2-[(3-dimethylamino-propyl)-methyl-carbamoyl]-3-methyl-butyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-Cyclohexylmethyl-5-{(S)-2-[(3-dimethylamino-propyl)-methyl-carbamoyl]-3-methyl-butyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 1 articles about (4S,5S)-4-Cyclohexylmethyl-5-{(S)-2-[(3-dimethylamino-propyl)-methyl-carbamoyl]-3-methyl-butyl}-2,2-dimethyl-oxazolidine-3-carboxylic 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:

2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanoic acid (129921-93-3) + N,N,N'-trimethylpropane-1,3-diamine (4543-96-8) → (4S,5S)-4-Cyclohexylmethyl-5-{(S)-2-[(3-dimethylamino-propyl)-methyl-carbamoyl]-3-methyl-butyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (140660-89-5)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Yield given. Multistep reaction; 1 a.) DMF, from -20 deg C to 0 deg C, 1 h, b.) 0 deg C, 24 h, 2 a.) DMF, 0 deg C, 4 h, b.) from 0 deg C to RT, 20 h;

DOI:10.1021/jm00088a007

Reference yield:

(4S,5S)-4-Cyclohexylmethyl-5-{(S)-2-[(3-dimethylamino-propyl)-methyl-carbamoyl]-3-methyl-butyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (140660-89-5) → (2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide (140660-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / 1.) CH₂Cl₂, from -10 deg C to 0 deg C, 4 h,2.) THF, water, RT, 18 h

2: HOBT, N-methylmorpholine, EDC / dimethylformamide / 24 h / Ambient temperature

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm00088a007

Reference yield:

(4S,5S)-4-Cyclohexylmethyl-5-{(S)-2-[(3-dimethylamino-propyl)-methyl-carbamoyl]-3-methyl-butyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (140660-89-5) → (2S,4S,5S)-5-Amino-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide

Guidance literature:

With trifluoroacetic acid; Multistep reaction; 1.) CH₂Cl₂, from -10 deg C to 0 deg C, 4 h,2.) THF, water, RT, 18 h;

DOI:10.1021/jm00088a007

upstream raw materials:

2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanoic acid

N,N,N'-trimethylpropane-1,3-diamine

Downstream raw materials:

(2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide