{(S)-1-[Hydroxy-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester

Base Information

• Chemical Name: {(S)-1-[Hydroxy-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester
• CAS No.: 865537-78-6
• Molecular Formula: C₁₉H₃₃N₃O₄
• Molecular Weight: 367.489

Synonyms:{(S)-1-[Hydroxy-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester

Chemical Property of {(S)-1-[Hydroxy-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester

Chemical Property:

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Technology Process of {(S)-1-[Hydroxy-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester

There total 11 articles about {(S)-1-[Hydroxy-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl 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: 87.0%

{(S)-1-[(tert-Butyl-dimethyl-silanyloxy)-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester (865537-77-5) → {(S)-1-[Hydroxy-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester (865537-78-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.05.091

Reference yield:

(S)-1-phenylpropan-2-ol (1517-68-6,14898-87-4) → {(S)-1-[Hydroxy-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester (865537-78-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 90 percent / H₂; Aliquat 336 / RhCl₃*H₂O

2: toluene; tetrahydrofuran / 0 - 20 °C

3: iPr₂NEt / toluene; tetrahydrofuran

4: 87 percent / LiOH / tetrahydrofuran

5: N-methylmorpholine / tetrahydrofuran

6: sodium borohydride / tetrahydrofuran

7: sulfur trioxide pyridine complex / CH₂Cl₂

8: 18-crown-6; KCN / CH₂Cl₂

9: hydroxylamine; sodium acetate

10: toluene / Heating

11: 87 percent / TBAF / tetrahydrofuran

With 4-methyl-morpholine; potassium cyanide; lithium hydroxide; sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydrogen; hydroxylamine; sodium acetate; sulfur trioxide pyridine complex; Aliquat 336; N-ethyl-N,N-diisopropylamine; rhodium(III) chloride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.bmcl.2005.05.091

Reference yield:

(S)-2-((S)-2-Cyclohexyl-1-methyl-ethoxycarbonylamino)-hexanoic acid (865537-75-3) → {(S)-1-[Hydroxy-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester (865537-78-6)

Guidance literature:

Multi-step reaction with 7 steps

1: N-methylmorpholine / tetrahydrofuran

2: sodium borohydride / tetrahydrofuran

3: sulfur trioxide pyridine complex / CH₂Cl₂

4: 18-crown-6; KCN / CH₂Cl₂

5: hydroxylamine; sodium acetate

6: toluene / Heating

7: 87 percent / TBAF / tetrahydrofuran

With 4-methyl-morpholine; potassium cyanide; sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydroxylamine; sodium acetate; sulfur trioxide pyridine complex; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.bmcl.2005.05.091

upstream raw materials:

{(S)-1-[(tert-Butyl-dimethyl-silanyloxy)-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester

(S)-2-((S)-2-Cyclohexyl-1-methyl-ethoxycarbonylamino)-hexanoic acid

(S)-2-((S)-2-Cyclohexyl-1-methyl-ethoxycarbonylamino)-hexanoic acid methyl ester

{(S)-1-[(tert-Butyl-dimethyl-silanyloxy)-cyano-methyl]-pentyl}-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester

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