(2Z)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide

Base Information

• Chemical Name: (2Z)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide
• CAS No.: 118741-17-6
• Molecular Formula: C₂₆H₄₀N₂O₄
• Molecular Weight: 444.615
• Mol file: 118741-17-6.mol

Synonyms:(2Z)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide

Chemical Property of (2Z)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide

There total 12 articles about (2Z)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide 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: 27.0%

isobutylamine (78-81-9) + 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2-propenoic acid (130981-00-9) → (2Z)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide (118741-17-6) + (2E)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide (118741-18-7)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In N,N-dimethyl-formamide; at -10 ℃; for 1h;

DOI:10.1246/bcsj.63.2224

Reference yield:

statine (49642-07-1) → (2Z)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide (118741-17-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / Et₃N / dioxane; H₂O / 30 °C

2: HCl / 1) r.t., 24h, 2) 40 deg C, 24h

3: 91 percent / p-toluenesulfonic acid / 1) r.t., 2h, 2) 38 deg C_., 1h

4: 99.7 percent / NaBH₄ / ethanol

5: pyridine / Ambient temperature

6: 99 percent / t-BuOK, DMSO / benzene / 0.17 h / Ambient temperature

7: 94 percent / osmium tetroxide / dioxane / 0.25 h / Ambient temperature

8: 88 percent / LiCl, DBU / tetrahydrofuran / Ambient temperature

9: KOH, EtOH-water 9:1 / 3 h / Ambient temperature

10: 37 percent / diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1 h / -10 °C

With pyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; ethanol; diphenyl phosphoryl azide; potassium tert-butylate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; benzene;

DOI:10.1246/bcsj.63.2224

Reference yield:

(3S,4S)-4-(carbamic acid benzyl ester)-3-hydroxy-6-methyl-heptanoic acid (93287-37-7) → (2Z)-N-Isobutyl-3-<(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyl-5-oxazolidinyl>-2-ethyl-2-propenamide (118741-17-6)

Guidance literature:

Multi-step reaction with 9 steps

1: HCl / 1) r.t., 24h, 2) 40 deg C, 24h

2: 91 percent / p-toluenesulfonic acid / 1) r.t., 2h, 2) 38 deg C_., 1h

3: 99.7 percent / NaBH₄ / ethanol

4: pyridine / Ambient temperature

5: 99 percent / t-BuOK, DMSO / benzene / 0.17 h / Ambient temperature

6: 94 percent / osmium tetroxide / dioxane / 0.25 h / Ambient temperature

7: 88 percent / LiCl, DBU / tetrahydrofuran / Ambient temperature

8: KOH, EtOH-water 9:1 / 3 h / Ambient temperature

9: 37 percent / diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1 h / -10 °C

With pyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; ethanol; diphenyl phosphoryl azide; potassium tert-butylate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl-formamide; benzene;

DOI:10.1246/bcsj.63.2224

upstream raw materials:

isobutylamine

3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-ethyl-2-propenoic acid

statine

(4S,5S)-3-Benzyloxycarbonyl-5-ethenyl-4-isobutyl-2,2-dimethyloxazolidine