Technology Process of (9S,12S,15S)-12-(2-Amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylic acid
There total 19 articles about (9S,12S,15S)-12-(2-Amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylic acid which
guide to synthetic route it.
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synthetic route:
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129151-11-7
(9S,12S,15S)-12-(2-Amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylic acid
- Guidance literature:
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Multi-step reaction with 11 steps
1: 70 percent / CBr4, Ph3P / diethyl ether / 12 h / 25 °C
2: NaH / tetrahydrofuran / 1.) 0 deg C, 20 min; 2.) -78 deg C, 12 h
3: 0.5 N aq. HCl / tetrahydrofuran / 14 h / 25 °C
4: 88 percent / EDCI, HOBt / dimethylformamide / 12 h / 25 °C
5: H2 / Pd-C / tetrahydrofuran / 3 h / 25 °C
6: NaHCO3 / tetrahydrofuran / 25 °C
7: 90 percent / n-Bu4NF / dimethylformamide / 4 h / 25 °C
8: 3.0 M HCl / ethyl acetate / 0.5 h / 25 °C
9: 58 percent / DPPA, NaHCO3 / dimethylformamide / 72 h / 0 °C
10: diethyl ether / 0 °C
11: 92 percent / LiOH, H2O / tetrahydrofuran; methanol / 25 °C
With
hydrogenchloride; lithium hydroxide; carbon tetrabromide; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)93447-1
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129151-11-7
(9S,12S,15S)-12-(2-Amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylic acid
- Guidance literature:
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Multi-step reaction with 12 steps
1: 86 percent / EDCI, HOBt / CH2Cl2 / 12 h / 25 °C
2: 70 percent / CBr4, Ph3P / diethyl ether / 12 h / 25 °C
3: NaH / tetrahydrofuran / 1.) 0 deg C, 20 min; 2.) -78 deg C, 12 h
4: 0.5 N aq. HCl / tetrahydrofuran / 14 h / 25 °C
5: 88 percent / EDCI, HOBt / dimethylformamide / 12 h / 25 °C
6: H2 / Pd-C / tetrahydrofuran / 3 h / 25 °C
7: NaHCO3 / tetrahydrofuran / 25 °C
8: 90 percent / n-Bu4NF / dimethylformamide / 4 h / 25 °C
9: 3.0 M HCl / ethyl acetate / 0.5 h / 25 °C
10: 58 percent / DPPA, NaHCO3 / dimethylformamide / 72 h / 0 °C
11: diethyl ether / 0 °C
12: 92 percent / LiOH, H2O / tetrahydrofuran; methanol / 25 °C
With
hydrogenchloride; lithium hydroxide; carbon tetrabromide; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)93447-1
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129151-11-7
(9S,12S,15S)-12-(2-Amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylic acid
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 92 percent / LiOH, H2O / tetrahydrofuran; methanol
2: 86 percent / EDCI, HOBt / CH2Cl2 / 12 h / 25 °C
3: 70 percent / CBr4, Ph3P / diethyl ether / 12 h / 25 °C
4: NaH / tetrahydrofuran / 1.) 0 deg C, 20 min; 2.) -78 deg C, 12 h
5: 0.5 N aq. HCl / tetrahydrofuran / 14 h / 25 °C
6: 88 percent / EDCI, HOBt / dimethylformamide / 12 h / 25 °C
7: H2 / Pd-C / tetrahydrofuran / 3 h / 25 °C
8: NaHCO3 / tetrahydrofuran / 25 °C
9: 90 percent / n-Bu4NF / dimethylformamide / 4 h / 25 °C
10: 3.0 M HCl / ethyl acetate / 0.5 h / 25 °C
11: 58 percent / DPPA, NaHCO3 / dimethylformamide / 72 h / 0 °C
12: diethyl ether / 0 °C
13: 92 percent / LiOH, H2O / tetrahydrofuran; methanol / 25 °C
With
hydrogenchloride; lithium hydroxide; carbon tetrabromide; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)93447-1
