9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ethyl ester

Base Information

• Chemical Name: 9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ethyl ester
• CAS No.: 127070-77-3
• Molecular Formula: C₂₆H₂₅FN₂O₆
• Molecular Weight: 480.493
• Mol file: 127070-77-3.mol

Synonyms:9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ethyl ester

Chemical Property of 9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ethyl ester

There total 15 articles about 9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ethyl 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: 86.0%

(Z)-2-[4-(1-Benzyloxycarbonylamino-cyclopropyl)-2,3,5-trifluoro-benzoyl]-3-(2-hydroxy-1-methyl-ethylamino)-acrylic acid ethyl ester (127045-84-5) → 9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ethyl ester (127070-77-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 100 ℃; for 3h;

DOI:10.1248/cpb.42.2063

Reference yield:

2,3,4,5-tetrafluorobenzoic acid (1201-31-6) → 9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ethyl ester (127070-77-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 91 percent / thionyl chloride / 1 h / Heating

2: NaH / dimethylformamide / 12 h / Ambient temperature

3: 1.) TFA / 1.) RT, 20 h, 2.) toluene, reflux, 2 h

4: 91 percent / diethyl ether; petroleum ether / Ambient temperature

5: 95 percent / acetic anhydride / dimethylsulfoxide / 2 h / Ambient temperature

6: 69 percent / dimethylsulfoxide / 0.5 h / 15 - 20 °C

7: 92 percent / TFA, anisole / 2 h / Ambient temperature

8: Et₃N / acetone / 1.5 h / -25 - -20 °C

9: NaN₃ / H₂O; acetone / 0.5 h / 5 °C

10: dioxane / 2 h / Heating

11: 92 percent / 1 N aq. NaOH / ethanol; dioxane / 2 h / Ambient temperature

12: tetrahydrofuran / 1 h / Ambient temperature

13: tetrahydrofuran / 20 h / Ambient temperature

14: 1.) benzene, reflux, 30 min, 2.) toluene, RT, 17 h

15: 86 percent / K₂CO₃ / dimethylformamide / 3 h / 90 - 100 °C

With sodium hydroxide; thionyl chloride; sodium azide; acetic anhydride; sodium hydride; potassium carbonate; methoxybenzene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; Petroleum ether;

DOI:10.1248/cpb.42.2063

Reference yield:

ethyl 2,3,4,5-tetrafluorobenzenecarboxylate (122894-73-9) → 9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ethyl ester (127070-77-3)

Guidance literature:

Multi-step reaction with 14 steps

1: NaH / dimethylformamide / 12 h / Ambient temperature

2: 1.) TFA / 1.) RT, 20 h, 2.) toluene, reflux, 2 h

3: 91 percent / diethyl ether; petroleum ether / Ambient temperature

4: 95 percent / acetic anhydride / dimethylsulfoxide / 2 h / Ambient temperature

5: 69 percent / dimethylsulfoxide / 0.5 h / 15 - 20 °C

6: 92 percent / TFA, anisole / 2 h / Ambient temperature

7: Et₃N / acetone / 1.5 h / -25 - -20 °C

8: NaN₃ / H₂O; acetone / 0.5 h / 5 °C

9: dioxane / 2 h / Heating

10: 92 percent / 1 N aq. NaOH / ethanol; dioxane / 2 h / Ambient temperature

11: tetrahydrofuran / 1 h / Ambient temperature

12: tetrahydrofuran / 20 h / Ambient temperature

13: 1.) benzene, reflux, 30 min, 2.) toluene, RT, 17 h

14: 86 percent / K₂CO₃ / dimethylformamide / 3 h / 90 - 100 °C

With sodium hydroxide; sodium azide; acetic anhydride; sodium hydride; potassium carbonate; methoxybenzene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; Petroleum ether;

DOI:10.1248/cpb.42.2063

upstream raw materials:

(Z)-2-[4-(1-Benzyloxycarbonylamino-cyclopropyl)-2,3,5-trifluoro-benzoyl]-3-(2-hydroxy-1-methyl-ethylamino)-acrylic acid ethyl ester

2,3,4,5-tetrafluorobenzoic acid

ethyl 2,3,4,5-tetrafluorobenzenecarboxylate

ethyl 4-carboxymethyl-2,3,5-trifluorobenzoate

Downstream raw materials:

10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid

10-(1-aminocyclopropyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid

Refernces