4-[2-tert-butoxycarbonylamino-2-(methoxy-methyl-carbamoyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-[2-tert-butoxycarbonylamino-2-(methoxy-methyl-carbamoyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 195877-91-9
• Molecular Formula: C₂₃H₃₅N₃O₆
• Molecular Weight: 449.547

Synonyms:4-[2-tert-butoxycarbonylamino-2-(methoxy-methyl-carbamoyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester

Chemical Property of 4-[2-tert-butoxycarbonylamino-2-(methoxy-methyl-carbamoyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of 4-[2-tert-butoxycarbonylamino-2-(methoxy-methyl-carbamoyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester

There total 8 articles about 4-[2-tert-butoxycarbonylamino-2-(methoxy-methyl-carbamoyl)-ethyl]-piperidine-1-carboxylic acid benzyl 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: 62.0%

3-{1-[(benzyloxy)carbonyl]piperidin-4-yl}-N-(tert-butoxycarbonyl)alanine (195877-90-8) + N,0-dimethylhydroxylamine (1117-97-1) → 4-[2-tert-butoxycarbonylamino-2-(methoxy-methyl-carbamoyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester (195877-91-9)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0960-894X(99)00179-1

Reference yield:

4-(Chloromethyl)pyridine (10445-91-7) → 4-[2-tert-butoxycarbonylamino-2-(methoxy-methyl-carbamoyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester (195877-91-9)

Guidance literature:

Multi-step reaction with 8 steps

1: NaOEt

2: 100 percent / aq. KOH / ethanol / 1 h / Ambient temperature

3: 67 percent / dimethylformamide / 1.5 h / Heating

4: 100 percent / H₂, aq. HCl / 10 percent Pd/C / ethanol

5: 100 percent / 6 N HCl / 4 h / Heating

6: CuSO₄, pH 9 / dioxane; H₂O / 16 h / Ambient temperature

7: pH 12.5 / 20 h / Ambient temperature

8: 62 percent / TBTU, Et₃N, pH 8.5 / CH₂Cl₂ / 2 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; hydrogen; sodium ethanolate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; copper(II) sulfate; triethylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(99)00179-1

Reference yield:

diethyl 2-(acetylamino)-2-(4-pyridinylmethyl)-malonate (89662-45-3) → 4-[2-tert-butoxycarbonylamino-2-(methoxy-methyl-carbamoyl)-ethyl]-piperidine-1-carboxylic acid benzyl ester (195877-91-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / aq. KOH / ethanol / 1 h / Ambient temperature

2: 67 percent / dimethylformamide / 1.5 h / Heating

3: 100 percent / H₂, aq. HCl / 10 percent Pd/C / ethanol

4: 100 percent / 6 N HCl / 4 h / Heating

5: CuSO₄, pH 9 / dioxane; H₂O / 16 h / Ambient temperature

6: pH 12.5 / 20 h / Ambient temperature

7: 62 percent / TBTU, Et₃N, pH 8.5 / CH₂Cl₂ / 2 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; copper(II) sulfate; triethylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(99)00179-1

upstream raw materials:

3-{1-[(benzyloxy)carbonyl]piperidin-4-yl}-N-(tert-butoxycarbonyl)alanine

N,0-dimethylhydroxylamine

4-(Chloromethyl)pyridine

diethyl 2-(acetylamino)-2-(4-pyridinylmethyl)-malonate

Downstream raw materials:

4-(2-tert-butoxycarbonylamino-3-oxo-3-thiazol-2-yl-propyl)-piperidine-1-carboxylic acid benzyl ester

4-(2-{[(S)-1-((R)-3-Cyclohexyl-2-ethanesulfonylamino-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-oxo-3-thiazol-2-yl-propyl)-piperidine-1-carboxylic acid benzyl ester

4-(2-amino-3-oxo-3-thiazol-2-yl-propyl)-piperidine-1-carboxylic acid benzyl ester

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