N-butyl-2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanamide

Base Information

• Chemical Name: N-butyl-2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanamide
• CAS No.: 129921-94-4
• Molecular Formula: C₂₇H₅₀N₂O₄
• Molecular Weight: 466.705
• Mol file: 129921-94-4.mol

Synonyms:N-butyl-2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanamide

Chemical Property of N-butyl-2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-butyl-2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanamide

There total 24 articles about N-butyl-2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanamide 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: 70.0%

(4S,5S)-5-((Z)-2-Butylcarbamoyl-3-methyl-but-1-enyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (141258-90-4) → N-butyl-2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanamide (129921-94-4) + (4S,5S)-5-((R)-2-Butylcarbamoyl-3-methyl-butyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (131316-86-4)

Guidance literature:

With hydrogen; Rh/Al₂O₃; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)91634-4

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → N-butyl-2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanamide (129921-94-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 98 percent / H₂ / PtO₂ / ethanol

2: 95 percent / 1,1'-carbonyldiimidazole, Et₃N / tetrahydrofuran

3: 93 percent / LiAlH₄ / diethyl ether

4: 1) n-BuLi, 2) ZnBr₂ / 1) THF, 2) THF

5: 78 percent / PpTSA / CH₂Cl₂

6: 80 percent / RuCl₃*H₂O, NaIO₄ / acetonitrile; CCl₄; H₂O

7: 80 percent / 1,1'-carbonyldiimidazole, Et₃N / tetrahydrofuran

8: 95 percent / LiAlH₄ / diethyl ether

9: 81 percent / KN(TMS)2 / tetrahydrofuran

10: 88 percent / Me₃Al / 1,2-dichloro-ethane

11: 70 percent / H₂ / Rh/Al₂O₃ / tetrahydrofuran

With ruthenium trichloride; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; hydrogen; trimethylaluminum; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; triethylamine; 1,1'-carbonyldiimidazole; zinc dibromide; platinum(IV) oxide; Rh/Al₂O₃; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4039(00)91634-4

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid (37736-82-6) → N-butyl-2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanamide (129921-94-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / 1,1'-carbonyldiimidazole, Et₃N / tetrahydrofuran

2: 93 percent / LiAlH₄ / diethyl ether

3: 1) n-BuLi, 2) ZnBr₂ / 1) THF, 2) THF

4: 78 percent / PpTSA / CH₂Cl₂

5: 80 percent / RuCl₃*H₂O, NaIO₄ / acetonitrile; CCl₄; H₂O

6: 80 percent / 1,1'-carbonyldiimidazole, Et₃N / tetrahydrofuran

7: 95 percent / LiAlH₄ / diethyl ether

8: 81 percent / KN(TMS)2 / tetrahydrofuran

9: 88 percent / Me₃Al / 1,2-dichloro-ethane

10: 70 percent / H₂ / Rh/Al₂O₃ / tetrahydrofuran

With ruthenium trichloride; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; hydrogen; trimethylaluminum; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; triethylamine; 1,1'-carbonyldiimidazole; zinc dibromide; Rh/Al₂O₃; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4039(00)91634-4

upstream raw materials:

(4S,5S)-5-((Z)-2-Butylcarbamoyl-3-methyl-but-1-enyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

N-butylamine

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid

Downstream raw materials:

(2R,4S,5S)-5-amino-N-butyl-6-cyclohexyl-4-hydroxy-2-isopropylhexanamide

(2S,4S,5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2-isopropyl-N-butylhexanamide

(2S,4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-2-isopropyl hexanoic acid n-butyl amide