ethyl 1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-carboxylate

Base Information

Chemical Name:ethyl 1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-carboxylate
CAS No.:318987-58-5
Molecular Formula:C₃₁H₃₂ClN₃O₈S
Molecular Weight:642.129
Hs Code.:

ethyl 1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-carboxylate

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Chemical Property of ethyl 1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-carboxylate

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Technology Process of ethyl 1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-carboxylate

There total 9 articles about ethyl 1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-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: 61.0%

: 64-17-5
ethanol

: 318987-57-4
1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-carboxylic acid

: 318987-58-5
ethyl 1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-carboxylate

Guidance literature:: With pyridine; p-toluenesulfonyl chloride; at 20 ℃; for 4h;
DOI:10.1248/cpb.52.406

Reference yield:

: 318987-57-4
1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-carboxylic acid

: 318987-58-5
ethyl 1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-carboxylate

Guidance literature:: With ethanol; p-toluenesulfonyl chloride; In pyridine; at 20 ℃; for 4h;

Reference yield:

: 102153-63-9
6-chloronaphth-2-ylsulfonyl chloride

: 318987-58-5
ethyl 1'-benzyloxycarbonyl-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-5-oxo-spiro[8aH-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidine]-8a-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

2: 81 percent / K₂CO₃; NaI / dimethylformamide / 1.5 h / 20 °C

3: 50 percent / p-toluenesulfonic acid monohydrate / toluene / 1 h / Heating

4: 1,8-bis(N,N-dimethylamino)naphthalene / 1,2-dichloro-ethane / 2 h / 20 °C

5: 67.9 g / aq. NaOH / methanol; CH₂Cl₂ / 0.5 h / 20 °C

6: 90 percent / 4-benzyloxy-2,2,6,6-tetramethylpiperidine 1-oxyl; aq. NaHCO₃ / CH₂Cl₂ / 1.5 h / cooling

7: 61 percent / pyridine; p-toluenesulfonyl chloride / 4 h / 20 °C

With pyridine; sodium hydroxide; 4-hydroxy-TEMPO benzoate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; p-toluenesulfonyl chloride; sodium iodide; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.52.406