C₁₄H₁₅N₃O₆

Base Information

• Chemical Name: C₁₄H₁₅N₃O₆
• CAS No.: 138125-69-6
• Molecular Formula: C₁₄H₁₅N₃O₆
• Molecular Weight: 321.29
• Mol file: 138125-69-6.mol

Synonyms:

Chemical Property of C₁₄H₁₅N₃O₆

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₁₄H₁₅N₃O₆

There total 33 articles about C₁₄H₁₅N₃O₆ 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: 95.0%

C14H12N2O6 (137964-95-5) → C14H15N3O6 (102363-08-6,108814-62-6,108814-63-7,138125-68-5,138125-69-6)

Guidance literature:

With ammonia; In dichloromethane; at 23 ℃; for 2h;

DOI:10.1021/ja00027a071

Reference yield:

2-Amino-6-hydroxy-4-methyl-benzoic acid ethyl ester → C14H15N3O6 (102363-08-6,108814-62-6,108814-63-7,138125-68-5,138125-69-6)

Guidance literature:

Multi-step reaction with 32 steps

1: 1.) aq. NaNO₂, HCl, 2.) NaN₃ / 1.) EtOH, 0 deg C, 20 min, 2.) EtOH, 0 deg C, 40 min

2: i-Pr₂NEt / CH₂Cl₂ / 23 °C

3: NBS, Bz₂O₂ / benzene / 2 h / Heating

4: K₂CO₃ / dimethylformamide / 0.25 h / 70 °C

5: TFA / CH₂Cl₂ / 3 h / 23 °C

6: K₂CO₃ / dimethylformamide / 80 °C

7: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

8: 98 percent / PCC / CH₂Cl₂ / 23 °C

9: toluene / 7 h / 170 °C

10: NaOH / methanol / 23 °C

11: m-CPBA / 4 h / 23 °C

12: ClCOCOCl, DMSO (Swern oxidation)

13: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

14: NaBH₄ / ethanol / -78 - 23 °C

15: 92 percent / imidazole, DMAP / CH₂Cl₂ / 23 °C

16: 64 percent / DIBAL / toluene / -78 °C

17: m-CPBA / CH₂Cl₂ / 23 °C

18: 10 h / 23 °C

19: 83 percent / ClCOCOCl, DMSO (Swern oxidation)

20: H₂NNH₂ / methanol; CH₂Cl₂ / 23 °C

21: n-Bu₄NF / tetrahydrofuran / 23 °C

22: 100 percent / CSA / CH₂Cl₂ / 23 °C

23: aq. NaN₃ / dimethylformamide / 6 h / 125 °C

24: Et₃N / CH₂Cl₂ / 23 °C

25: 1.) TFA, 2.) COCl₂, pyridine / 1.) CH₂Cl₂, 23 deg C, 10 min, 2.) CH₂Cl₂, 23 deg C

26: ceric ammonium nitrate (CAN) / acetonitrile; H₂O / 23 °C

27: PCC, MgSO₄ / CH₂Cl₂ / 23 °C

28: CSA / methanol / 23 °C

29: 71 percent / Ph₃P, i-Pr₂NEt / tetrahydrofuran; H₂O / 0.5 h / 60 °C

30: 100 percent / H₂ / Pd/C / ethanol / 2 h / 23 °C / 760 Torr

31: 96 percent / aq. HClO₄ / tetrahydrofuran / 2 h / 23 °C

32: 95 percent / NH₃ / CH₂Cl₂ / 2 h / 23 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; perchloric acid; oxalyl dichloride; ammonium cerium(IV) nitrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; hydrogen; diisobutylaluminium hydride; magnesium sulfate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; hydrazine; sodium nitrite; dibenzoyl peroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1021/ja00027a071

Reference yield:

2-Azido-6-hydroxy-4-methyl-benzoic acid ethyl ester → C14H15N3O6 (102363-08-6,108814-62-6,108814-63-7,138125-68-5,138125-69-6)

Guidance literature:

Multi-step reaction with 31 steps

1: i-Pr₂NEt / CH₂Cl₂ / 23 °C

2: NBS, Bz₂O₂ / benzene / 2 h / Heating

3: K₂CO₃ / dimethylformamide / 0.25 h / 70 °C

4: TFA / CH₂Cl₂ / 3 h / 23 °C

5: K₂CO₃ / dimethylformamide / 80 °C

6: 100 percent / DIBAL / CH₂Cl₂ / -78 °C

7: 98 percent / PCC / CH₂Cl₂ / 23 °C

8: toluene / 7 h / 170 °C

9: NaOH / methanol / 23 °C

10: m-CPBA / 4 h / 23 °C

11: ClCOCOCl, DMSO (Swern oxidation)

12: aq. LiOH / tetrahydrofuran / 2 h / 0 °C

13: NaBH₄ / ethanol / -78 - 23 °C

14: 92 percent / imidazole, DMAP / CH₂Cl₂ / 23 °C

15: 64 percent / DIBAL / toluene / -78 °C

16: m-CPBA / CH₂Cl₂ / 23 °C

17: 10 h / 23 °C

18: 83 percent / ClCOCOCl, DMSO (Swern oxidation)

19: H₂NNH₂ / methanol; CH₂Cl₂ / 23 °C

20: n-Bu₄NF / tetrahydrofuran / 23 °C

21: 100 percent / CSA / CH₂Cl₂ / 23 °C

22: aq. NaN₃ / dimethylformamide / 6 h / 125 °C

23: Et₃N / CH₂Cl₂ / 23 °C

24: 1.) TFA, 2.) COCl₂, pyridine / 1.) CH₂Cl₂, 23 deg C, 10 min, 2.) CH₂Cl₂, 23 deg C

25: ceric ammonium nitrate (CAN) / acetonitrile; H₂O / 23 °C

26: PCC, MgSO₄ / CH₂Cl₂ / 23 °C

27: CSA / methanol / 23 °C

28: 71 percent / Ph₃P, i-Pr₂NEt / tetrahydrofuran; H₂O / 0.5 h / 60 °C

29: 100 percent / H₂ / Pd/C / ethanol / 2 h / 23 °C / 760 Torr

30: 96 percent / aq. HClO₄ / tetrahydrofuran / 2 h / 23 °C

31: 95 percent / NH₃ / CH₂Cl₂ / 2 h / 23 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; perchloric acid; oxalyl dichloride; ammonium cerium(IV) nitrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; hydrogen; diisobutylaluminium hydride; magnesium sulfate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; hydrazine; dibenzoyl peroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1021/ja00027a071

upstream raw materials:

C₁₄H₁₂N₂O₆

2-Benzylamino-6-hydroxy-4-methyl-benzoic acid ethyl ester

2-Azido-6-methoxymethoxy-4-methyl-benzoic acid ethyl ester

2-Azido-6-methoxymethoxy-4-(4-methoxy-phenoxymethyl)-benzoic acid ethyl ester