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

Base Information

Chemical Name:N-butyl-2(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(R)-oxazolidinyl)-(R)-hydroxymethyl)-3-methylbutanamide
CAS No.:129921-97-7
Molecular Formula:C₂₇H₅₀N₂O₅
Molecular Weight:482.704
Hs Code.:

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

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

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

There total 9 articles about N-butyl-2(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(R)-oxazolidinyl)-(R)-hydroxymethyl)-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: 78.0%

: 129921-96-6
3-(3(R)-(3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(R)-oxazolidinyl)-3-hydroxy-2(R)-isopropyl-1-oxopropyl)-4(S)-(methoxycarbonyl)-1,3-thiazolidine-2-thione

: 109-73-9,85404-21-3
N-butylamine

: 129921-97-7
N-butyl-2(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(R)-oxazolidinyl)-(R)-hydroxymethyl)-3-methylbutanamide

Guidance literature:: In acetonitrile; for 1h; Ambient temperature;
DOI:10.1021/jo00001a083

Reference yield:

: 108-12-3
isopentanoyl chloride

: 129921-97-7
N-butyl-2(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(R)-oxazolidinyl)-(R)-hydroxymethyl)-3-methylbutanamide

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / pyridine / CH₂Cl₂ / 1.) -78 deg C, 1 h 2.) -78 deg C to r.t., 30 min

3: 78 percent / acetonitrile / 1 h / Ambient temperature

With pyridine; In dichloromethane; acetonitrile;
DOI:10.1021/jo00001a083

Reference yield:

: 112190-41-7,117997-58-7,122292-90-4,122292-91-5,127306-04-1
(4R,5R)-4-Cyclohexylmethyl-5-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 129921-97-7,138663-79-3
(4R,5S)-5-((1R,2S)-2-Butylcarbamoyl-1-hydroxy-3-methyl-butyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 60 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 °C

2: LiOH, H₂O / tetrahydrofuran / 18 h / Ambient temperature

3: EDC, 1-hydroxybenzotriazole, N-methylmorpholine / dimethylformamide / 24 h / 0 °C

4: 16 h / 0 deg C -> r. t.

With 4-methyl-morpholine; lithium hydroxide; boron trifluoride diethyl etherate; water; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(91)80205-K