(S)-2-(2,4-Dimethoxy-benzylamino)-5-((Z)-4-{(1S,2R)-2-[(E)-2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-vinyl]-cyclopentyl}-but-2-enoylamino)-pentanoic acid methyl ester

Base Information

• Chemical Name: (S)-2-(2,4-Dimethoxy-benzylamino)-5-((Z)-4-{(1S,2R)-2-[(E)-2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-vinyl]-cyclopentyl}-but-2-enoylamino)-pentanoic acid methyl ester
• CAS No.: 105835-36-7
• Molecular Formula: C₃₂H₄₄N₂O₈
• Molecular Weight: 584.71
• Mol file: 105835-36-7.mol

Synonyms:

Chemical Property of (S)-2-(2,4-Dimethoxy-benzylamino)-5-((Z)-4-{(1S,2R)-2-[(E)-2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-vinyl]-cyclopentyl}-but-2-enoylamino)-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(2,4-Dimethoxy-benzylamino)-5-((Z)-4-{(1S,2R)-2-[(E)-2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-vinyl]-cyclopentyl}-but-2-enoylamino)-pentanoic acid methyl ester

There total 17 articles about (S)-2-(2,4-Dimethoxy-benzylamino)-5-((Z)-4-{(1S,2R)-2-[(E)-2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-vinyl]-cyclopentyl}-but-2-enoylamino)-pentanoic acid methyl 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:

(1S,5S)-bicyclo<3.3.0>octan-2-one (85717-57-3) → (S)-2-(2,4-Dimethoxy-benzylamino)-5-((Z)-4-{(1S,2R)-2-[(E)-2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-vinyl]-cyclopentyl}-but-2-enoylamino)-pentanoic acid methyl ester (105835-36-7,105928-20-9)

Guidance literature:

Multi-step reaction with 12 steps

2: 1.) Amberlyst-15, 2.) Ph₃P / 1.) acetone, water, 25 deg C, 24 h, 2.) CH₂Cl₂, 0 deg c, 10 min

4: Amberlyst-15 / 2 h / 25 °C

5: 1.) n-BuLi / 1.) THF, -78 to 25 deg C, 2 h, 2.) THF, -78 to 25 deg C, 16 h

6: K₂CO₃ / methanol; H₂O / 3 h / 50 °C

7: 2,4,6-(CH₃)3PhSO₂Cl / tetrahydrofuran / 5 h / 25 °C

8: DMAP / tetrahydrofuran / 12 h / 25 °C

9: 1.) Amberlyst-15, 2.) t-BuOK / 1.) acetone, water, 25 deg C, 20 h, 2.) THF, 0 to 25 deg C, 12 h

10: 70 percent / (PPh₃)4Pd, Ph₃P, acetic acid / CH₂Cl₂ / 2 h / 25 °C

11: 100 percent / H₂, quinoline, acetic acid / 5percent Pd/BaSO₄ / ethyl acetate / 1.5 h / 25 °C / 760 Torr

12: 2.) NaCNBH₃ / 1.) 25 deg C, 16 h, 2.) CH₃OH, 25 deg C, 2 h

With quinoline; dmap; 2-mesitylenesulphonyl chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; amberlyst-15; potassium tert-butylate; hydrogen; sodium cyanoborohydride; potassium carbonate; acetic acid; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo00376a101

Reference yield:

Nδ-(tert-butoxycarbonyl)-L-ornithine (13650-49-2,184576-63-4) → (S)-2-(2,4-Dimethoxy-benzylamino)-5-((Z)-4-{(1S,2R)-2-[(E)-2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-vinyl]-cyclopentyl}-but-2-enoylamino)-pentanoic acid methyl ester (105835-36-7,105928-20-9)

Guidance literature:

Multi-step reaction with 8 steps

1: NaHCO₃ / H₂O; dioxane / 16 h / 0 °C

2: DCC, DMAP

3: CH₂Cl₂ / 0.5 h / 0 °C

4: DMAP / tetrahydrofuran / 12 h / 25 °C

5: 1.) Amberlyst-15, 2.) t-BuOK / 1.) acetone, water, 25 deg C, 20 h, 2.) THF, 0 to 25 deg C, 12 h

6: 70 percent / (PPh₃)4Pd, Ph₃P, acetic acid / CH₂Cl₂ / 2 h / 25 °C

7: 100 percent / H₂, quinoline, acetic acid / 5percent Pd/BaSO₄ / ethyl acetate / 1.5 h / 25 °C / 760 Torr

8: 2.) NaCNBH₃ / 1.) 25 deg C, 16 h, 2.) CH₃OH, 25 deg C, 2 h

With quinoline; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; amberlyst-15; potassium tert-butylate; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo00376a101

Reference yield:

L-ornithine hydrochloride (3184-13-2,36630-89-4) → (S)-2-(2,4-Dimethoxy-benzylamino)-5-((Z)-4-{(1S,2R)-2-[(E)-2-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-vinyl]-cyclopentyl}-but-2-enoylamino)-pentanoic acid methyl ester (105835-36-7,105928-20-9)

Guidance literature:

Multi-step reaction with 9 steps

2: NaHCO₃ / H₂O; dioxane / 16 h / 0 °C

3: DCC, DMAP

4: CH₂Cl₂ / 0.5 h / 0 °C

5: DMAP / tetrahydrofuran / 12 h / 25 °C

6: 1.) Amberlyst-15, 2.) t-BuOK / 1.) acetone, water, 25 deg C, 20 h, 2.) THF, 0 to 25 deg C, 12 h

7: 70 percent / (PPh₃)4Pd, Ph₃P, acetic acid / CH₂Cl₂ / 2 h / 25 °C

8: 100 percent / H₂, quinoline, acetic acid / 5percent Pd/BaSO₄ / ethyl acetate / 1.5 h / 25 °C / 760 Torr

9: 2.) NaCNBH₃ / 1.) 25 deg C, 16 h, 2.) CH₃OH, 25 deg C, 2 h

With quinoline; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; amberlyst-15; potassium tert-butylate; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo00376a101

upstream raw materials:

2,4-Dimethoxybenzaldehyde

(1S,5S)-bicyclo<3.3.0>octan-2-one

N^δ-(tert-butoxycarbonyl)-L-ornithine

L-ornithine hydrochloride