2-tert-butoxycarbonylamino-4-methoxy-3-oxo-butyric acid methyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-4-methoxy-3-oxo-butyric acid methyl ester
• CAS No.: 924288-31-3
• Molecular Formula: C₁₁H₁₉NO₆
• Molecular Weight: 261.275
• Mol file: 924288-31-3.mol

Synonyms:2-tert-butoxycarbonylamino-4-methoxy-3-oxo-butyric acid methyl ester

Chemical Property of 2-tert-butoxycarbonylamino-4-methoxy-3-oxo-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-tert-butoxycarbonylamino-4-methoxy-3-oxo-butyric acid methyl ester

There total 1 articles about 2-tert-butoxycarbonylamino-4-methoxy-3-oxo-butyric 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: 59.0%

Methoxyacetyl chloride (38870-89-2) + N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) → 2-tert-butoxycarbonylamino-4-methoxy-3-oxo-butyric acid methyl ester (924288-31-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 25 ℃; for 16h;

DOI:10.1002/anie.200602798

Reference yield:

2-tert-butoxycarbonylamino-4-methoxy-3-oxo-butyric acid methyl ester (924288-31-3) → C58H63N13O10S6Si (924288-59-5)

Guidance literature:

Multi-step reaction with 16 steps

1.1: LiBH₄ / tetrahydrofuran; CH₂Cl₂; methanol / 0.08 h / -78 °C

2.1: trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

3.1: HATU; i-Pr₂NEt / CH₂Cl₂ / 3 h / 25 °C

4.1: 77 percent / imidazole / dimethylformamide / 16 h / 20 °C

5.1: 66 percent / Lawesson reagent / tetrahydrofuran / 16 h / Heating

6.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h

7.1: N,N-diethylaminosulfur trifluoride / CH₂Cl₂ / 1 h / -78 °C

8.1: BrCCl₃; DBU / CH₂Cl₂ / 1 h / 0 °C

9.1: trifluoroacetic acid / CH₂Cl₂ / 1 h / 25 °C

10.1: HATU; i-Pr₂NEt / CH₂Cl₂ / 3 h / 25 °C

11.1: LiOH / methanol / 16 h / 25 °C

12.1: HATU; i-Pr₂NEt / CH₂Cl₂ / 24 h / 25 °C

13.1: Me₃SnOH / 1,2-dichloro-ethane / 16 h / 60 °C

13.2: trifluoroacetic acid / CH₂Cl₂ / 1 h / 25 °C

13.3: pentafluorophenyl diphenylphosphinate; i-Pr₂NEt / CH₂Cl₂; dimethylformamide / 24 h

14.1: Me₃SnOH / 1,2-dichloro-ethane / 5 h / 80 °C

15.1: HATU; i-Pr₂NEt / CH₂Cl₂ / 16 h / 25 °C

16.1: 85 percent / N,N-diethylaminosulfur trifluoride / CH₂Cl₂ / 1 h / -25 °C

With Lawessons reagent; 1H-imidazole; lithium hydroxide; lithium borohydride; Bromotrichloromethane; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trimethyltin(IV) hydroxide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200602798

Reference yield:

2-tert-butoxycarbonylamino-4-methoxy-3-oxo-butyric acid methyl ester (924288-31-3) → C61H72N12O12S6Si (924288-49-3)

Guidance literature:

Multi-step reaction with 12 steps

1: LiBH₄ / tetrahydrofuran; CH₂Cl₂; methanol / 0.08 h / -78 °C

2: trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

3: HATU; i-Pr₂NEt / CH₂Cl₂ / 3 h / 25 °C

4: 77 percent / imidazole / dimethylformamide / 16 h / 20 °C

5: 66 percent / Lawesson reagent / tetrahydrofuran / 16 h / Heating

6: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5 h

7: N,N-diethylaminosulfur trifluoride / CH₂Cl₂ / 1 h / -78 °C

8: BrCCl₃; DBU / CH₂Cl₂ / 1 h / 0 °C

9: trifluoroacetic acid / CH₂Cl₂ / 1 h / 25 °C

10: HATU; i-Pr₂NEt / CH₂Cl₂ / 3 h / 25 °C

11: LiOH / methanol / 16 h / 25 °C

12: HATU; i-Pr₂NEt / CH₂Cl₂ / 24 h / 25 °C

With Lawessons reagent; 1H-imidazole; lithium hydroxide; lithium borohydride; Bromotrichloromethane; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200602798

upstream raw materials:

Methoxyacetyl chloride

N-(tert-butoxycarbonyl)glycine methyl ester

Downstream raw materials:

C₅₅H₆₀N₁₂O₉S₆Si

C₅₂H₄₉N₁₃O₁₀S₆

C₅₈H₆₃N₁₃O₁₀S₆Si

C₆₁H₇₂N₁₂O₁₂S₆Si