(S)-1-[(3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

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Chemical Name:(S)-1-[(3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide
CAS No.:329259-25-8
Molecular Formula:C₃₉H₄₈FN₅O₄
Molecular Weight:669.84
Hs Code.:

(S)-1-[(3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

Synonyms:(S)-1-[(3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

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Chemical Property of (S)-1-[(3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

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Technology Process of (S)-1-[(3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

There total 24 articles about (S)-1-[(3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide 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: 68.0%

: 329259-23-6
(S)-1-[(2R,3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

: 329259-25-8
(S)-1-[(3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃;
DOI:10.1021/ol006931x

Reference yield:

: 62634-65-5
1-nitro-2-acetoxy-3-phenylpropane

: 329259-25-8
(S)-1-[(3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

Guidance literature:: Multi-step reaction with 17 steps

1.1: 73 percent / sodium carbonate / benzene / 4 h / Heating

2.1: LHMDS; LiCl / tetrahydrofuran; hexane / 1.3 h / -78 °C

2.2: 23 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.1: 88 percent / NaOH / 2-methyl-propan-2-ol; methanol; H₂O / 4 h / 75 °C

4.1: (COCl)2; DMF / CH₂Cl₂ / 0 - 23 °C

5.1: 55.2 mg / tetrahydrofuran; hexane / 2 h / 0 °C

6.1: 93 percent / aq. HBr; AcOH / 0.17 h / 0 °C

7.1: 75 percent / NaBH₄ / ethanol / 1.3 h / -78 °C

8.1: 93 percent / p-TsOH*H₂O / CH₂Cl₂ / 23 h / 23 °C

9.1: t-BuOK / 2-methyl-propan-2-ol / 0.05 h / 23 °C

9.2: KMnO₄; Na₂B₄O₇ / H₂O; 2-methyl-propan-2-ol / 1 h / 23 °C

10.1: EDC*HCl; 1-hydroxybenzotriazole / CH₂Cl₂ / 0.17 h / 23 °C

10.2: 39.3 mg / Et₃N / CH₂Cl₂ / 5.5 h / 23 °C

11.1: 91 percent / p-TsOH*H₂O / methanol / 3 h / 23 °C

12.1: 93 percent / CH₃SO₃H / ethyl acetate / 3 h / 23 °C

13.1: 94 percent / t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.2 h / 0 °C

14.1: 91 percent / propan-2-ol / 21 h / 80 °C

15.1: 94 percent / 1,4-cyclohexadiene / Pd/C / ethanol / 2 h / 23 °C

16.1: 80 percent / Et₃N / dimethylformamide / 13 h / 23 °C

17.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; methanesulfonic acid; cyclohexa-1,4-diene; potassium tert-butylate; hydrogen bromide; sodium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N-dimethyl-formamide; lithium chloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; tert-butyl alcohol; benzene; 17.1: Swern oxidation;
DOI:10.1021/ja010113y

Reference yield:

: 113361-26-5
(E)-3-phenyl-1-nitroprop-1-ene

: 329259-25-8
(S)-1-[(3S,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

Guidance literature:: Multi-step reaction with 16 steps

1.1: LHMDS; LiCl / tetrahydrofuran; hexane / 1.3 h / -78 °C

1.2: 23 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.1: 88 percent / NaOH / 2-methyl-propan-2-ol; methanol; H₂O / 4 h / 75 °C

3.1: (COCl)2; DMF / CH₂Cl₂ / 0 - 23 °C

4.1: 55.2 mg / tetrahydrofuran; hexane / 2 h / 0 °C

5.1: 93 percent / aq. HBr; AcOH / 0.17 h / 0 °C

6.1: 75 percent / NaBH₄ / ethanol / 1.3 h / -78 °C

7.1: 93 percent / p-TsOH*H₂O / CH₂Cl₂ / 23 h / 23 °C

8.1: t-BuOK / 2-methyl-propan-2-ol / 0.05 h / 23 °C

8.2: KMnO₄; Na₂B₄O₇ / H₂O; 2-methyl-propan-2-ol / 1 h / 23 °C

9.1: EDC*HCl; 1-hydroxybenzotriazole / CH₂Cl₂ / 0.17 h / 23 °C

9.2: 39.3 mg / Et₃N / CH₂Cl₂ / 5.5 h / 23 °C

10.1: 91 percent / p-TsOH*H₂O / methanol / 3 h / 23 °C

11.1: 93 percent / CH₃SO₃H / ethyl acetate / 3 h / 23 °C

12.1: 94 percent / t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.2 h / 0 °C

13.1: 91 percent / propan-2-ol / 21 h / 80 °C

14.1: 94 percent / 1,4-cyclohexadiene / Pd/C / ethanol / 2 h / 23 °C

15.1: 80 percent / Et₃N / dimethylformamide / 13 h / 23 °C

16.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; methanesulfonic acid; cyclohexa-1,4-diene; potassium tert-butylate; hydrogen bromide; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N-dimethyl-formamide; lithium chloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; tert-butyl alcohol; 16.1: Swern oxidation;
DOI:10.1021/ja010113y