isopropyl (S)-1-acetyl-2-benzyloxycarbonylhexahydropyridazine-3-carboxylate

Base Information

• Chemical Name: isopropyl (S)-1-acetyl-2-benzyloxycarbonylhexahydropyridazine-3-carboxylate
• CAS No.: 176237-47-1
• Molecular Formula: C₁₈H₂₄N₂O₅
• Molecular Weight: 348.399
• Mol file: 176237-47-1.mol

Synonyms:isopropyl (S)-1-acetyl-2-benzyloxycarbonylhexahydropyridazine-3-carboxylate

Chemical Property of isopropyl (S)-1-acetyl-2-benzyloxycarbonylhexahydropyridazine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of isopropyl (S)-1-acetyl-2-benzyloxycarbonylhexahydropyridazine-3-carboxylate

There total 5 articles about isopropyl (S)-1-acetyl-2-benzyloxycarbonylhexahydropyridazine-3-carboxylate 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: 84.0%

isopropyl (S)-2-(2-acetyl-1-benzyloxycarbonylhydrazino)-5-(methanesulfonyloxy)pentanoate (176237-46-0) → isopropyl (S)-1-acetyl-2-benzyloxycarbonylhexahydropyridazine-3-carboxylate (176237-47-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

DOI:10.1055/s-1996-4192

Reference yield:

(S)-N-Benzyloxycarbonylpyroglutamic acid chloride (61177-53-5) → isopropyl (S)-1-acetyl-2-benzyloxycarbonylhexahydropyridazine-3-carboxylate (176237-47-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridine / CH₂Cl₂ / -30 - 20 °C

2: 84 percent / NaBH₄, KH₂PO₄ / methanol; H₂O / 22 - 32 °C

3: 100 percent / NEt₃ / CH₂Cl₂ / 2 h / 0 °C

4: 1.) NaNO₂, Ac₂O, 2.) Zn, HOAc / 1.) HOAc, 0 deg C, 2.) 0 deg C, 3 h

5: 84 percent / NaH / dimethylformamide / 0.5 h / 0 °C

With pyridine; sodium tetrahydroborate; potassium dihydrogenphosphate; acetic anhydride; sodium hydride; acetic acid; triethylamine; zinc; sodium nitrite; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1055/s-1996-4192

Reference yield:

isopropyl (S)-2-(benzyloxycarbonylamino)-5-hydroxypentanoate (176237-44-8) → isopropyl (S)-1-acetyl-2-benzyloxycarbonylhexahydropyridazine-3-carboxylate (176237-47-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / NEt₃ / CH₂Cl₂ / 2 h / 0 °C

2: 1.) NaNO₂, Ac₂O, 2.) Zn, HOAc / 1.) HOAc, 0 deg C, 2.) 0 deg C, 3 h

3: 84 percent / NaH / dimethylformamide / 0.5 h / 0 °C

With acetic anhydride; sodium hydride; acetic acid; triethylamine; zinc; sodium nitrite; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1996-4192

upstream raw materials:

isopropyl (S)-2-(2-acetyl-1-benzyloxycarbonylhydrazino)-5-(methanesulfonyloxy)pentanoate

(S)-N-Benzyloxycarbonylpyroglutamic acid chloride

isopropyl (S)-2-(benzyloxycarbonylamino)-5-hydroxypentanoate

N-benzyloxycarbonyl-L-pyroglutamic acid isopropyl ester

Downstream raw materials:

(3S)-hexahydro-1,3-pridazinedicarboxylic acid 1-(phenylmethyl) ester