(11R,14S)-N-[(3-Fluoro-4-nitrophenyl)methyl]-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.110,14]heneicosa-3,5,16,18,19-pentaene-14-carboxamide

Base Information

Chemical Name:(11R,14S)-N-[(3-Fluoro-4-nitrophenyl)methyl]-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.110,14]heneicosa-3,5,16,18,19-pentaene-14-carboxamide
CAS No.:199486-38-9
Molecular Formula:C₃₂H₂₇FN₄O₇
Molecular Weight:598.587
Hs Code.:
DSSTox Substance ID:DTXSID101099520

(11R,14S)-N-[(3-Fluoro-4-nitrophenyl)methyl]-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.110,14]heneicosa-3,5,16,18,19-pentaene-14-carboxamide

Synonyms:DTXSID101099520;(11R,14S)-N-[(3-Fluoro-4-nitrophenyl)methyl]-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.110,14]heneicosa-3,5,16,18,19-pentaene-14-carboxamide;199486-38-9

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Chemical Property of (11R,14S)-N-[(3-Fluoro-4-nitrophenyl)methyl]-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.110,14]heneicosa-3,5,16,18,19-pentaene-14-carboxamide

Chemical Property:

XLogP3:4.2
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:4
Exact Mass:598.18637738
Heavy Atom Count:44
Complexity:1010

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:C1C(NC(=O)C(NC(=O)CC2=CC(=CC=C2)OC3=CC=C1C=C3)C4=CC=C(C=C4)O)C(=O)NCC5=CC(=C(C=C5)[N+](=O)[O-])F
Isomeric SMILES:C1[C@H](NC(=O)[C@H](NC(=O)CC2=CC(=CC=C2)OC3=CC=C1C=C3)C4=CC=C(C=C4)O)C(=O)NCC5=CC(=C(C=C5)[N+](=O)[O-])F

Technology Process of (11R,14S)-N-[(3-Fluoro-4-nitrophenyl)methyl]-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.110,14]heneicosa-3,5,16,18,19-pentaene-14-carboxamide

There total 16 articles about (11R,14S)-N-[(3-Fluoro-4-nitrophenyl)methyl]-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diazatricyclo[14.2.2.110,14]heneicosa-3,5,16,18,19-pentaene-14-carboxamide 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: 87.0%

: 199486-37-8
3-fluoro-4-nitrobenzylamine hydrochloride

: 199486-36-7
(11R,14S)-11-(4-Hydroxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid

: 199486-38-9
11(R)-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo-<14.2.2.1^3,7>heneicosa-1(19),3(21),4,6(20),17-hexaene-(14S)-14-carboxylic-3-fluoro-4-nitrobenzylamine

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane;
DOI:10.1016/S0040-4039(97)10217-9

Reference yield:

: 178744-40-6
(S)-2-[(R)-2-tert-Butoxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

: 199486-38-9
11(R)-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo-<14.2.2.1^3,7>heneicosa-1(19),3(21),4,6(20),17-hexaene-(14S)-14-carboxylic-3-fluoro-4-nitrobenzylamine

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) TFA, 2.) Et₃N, 3.) HOBT, EDC / 1) CH₂Cl₂, 0 deg C, 30 min; 2) CH₂Cl₂, 0 deg C, 10 min; 3) CH₂Cl₂, rt, 5 h

2: KHCO₃, 18-crown-6 ether / dimethylformamide / 10 h / Ambient temperature; further conditions

3: H₂ / Pd/C / methanol

4: t-BuONO / dimethylformamide / 0.25 h / 65 °C

5: 98 percent / aq. LiOH / tetrahydrofuran; methanol / 8 h

6: HOBT, EDC, Et₃N / dimethylformamide

With lithium hydroxide; tert.-butylnitrite; 18-crown-6 ether; hydrogen; benzotriazol-1-ol; potassium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(99)00171-4

Reference yield:

: 199486-35-6
(3S)-3-(4-fluoro-3-nitrophenyl)-2-<(2R)-2-(4-hydroxy-phenyl)-2-<2-(3-hydroxyphenyl)-acetylamino>acetylamino>-propionic acid methyl ester

: 199486-38-9
11(R)-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo-<14.2.2.1^3,7>heneicosa-1(19),3(21),4,6(20),17-hexaene-(14S)-14-carboxylic-3-fluoro-4-nitrobenzylamine

Guidance literature:: Multi-step reaction with 5 steps

1: KHCO₃, 18-crown-6 ether / dimethylformamide / 10 h / Ambient temperature; further conditions

2: H₂ / Pd/C / methanol

3: t-BuONO / dimethylformamide / 0.25 h / 65 °C

4: 98 percent / aq. LiOH / tetrahydrofuran; methanol / 8 h

5: HOBT, EDC, Et₃N / dimethylformamide

With lithium hydroxide; tert.-butylnitrite; 18-crown-6 ether; hydrogen; benzotriazol-1-ol; potassium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(99)00171-4