Methyl (9S,12S,15S)-12-(2-amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylate

Base Information

• Chemical Name: Methyl (9S,12S,15S)-12-(2-amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylate
• CAS No.: 127559-24-4
• Molecular Formula: C₃₂H₃₄N₄O₉
• Molecular Weight: 618.643

Synonyms:Methyl (9S,12S,15S)-12-(2-amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylate

Chemical Property of Methyl (9S,12S,15S)-12-(2-amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of Methyl (9S,12S,15S)-12-(2-amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylate

There total 39 articles about Methyl (9S,12S,15S)-12-(2-amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylate 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: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Methyl (9S,12S,15S)-12-(2-amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-hydroxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylate (127559-23-3) → Methyl (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-carboxylate (127559-24-4)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 ℃; for 12h;

DOI:10.1021/jo00311a019

Reference yield: 60.0%

3-{4-[5-(2-(S)-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-methoxyphenoxy]phenyl}-2-(S)-(2-(S)-tert-butoxycarbonylamino-3-carbamoylpropionylamino)propionic acid methyl ester (1192849-62-9) → Methyl (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-carboxylate (127559-24-4)

Guidance literature:

3-{4-[5-(2-(S)-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-methoxyphenoxy]phenyl}-2-(S)-(2-(S)-tert-butoxycarbonylamino-3-carbamoylpropionylamino)propionic acid methyl ester; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jo9018792

Reference yield:

sodium 4-iodo-benzoate (1005-30-7) → Methyl (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-carboxylate (127559-24-4)

Guidance literature:

Multi-step reaction with 14 steps

1: 51 percent / CuBr*Me₂S / nitrobenzene / 8 h / 130 °C

2: 89 percent / BH₃*THF / tetrahydrofuran / 3 h / 0 °C

3: 92 percent / LiOH, H₂O / tetrahydrofuran; methanol

4: 86 percent / EDCI, HOBt / CH₂Cl₂ / 12 h / 25 °C

5: 70 percent / CBr₄, Ph₃P / diethyl ether / 12 h / 25 °C

6: NaH / tetrahydrofuran / 1.) 0 deg C, 20 min; 2.) -78 deg C, 12 h

7: 0.5 N aq. HCl / tetrahydrofuran / 14 h / 25 °C

8: 88 percent / EDCI, HOBt / dimethylformamide / 12 h / 25 °C

9: H₂ / Pd-C / tetrahydrofuran / 3 h / 25 °C

10: NaHCO₃ / tetrahydrofuran / 25 °C

11: 90 percent / n-Bu₄NF / dimethylformamide / 4 h / 25 °C

12: 3.0 M HCl / ethyl acetate / 0.5 h / 25 °C

13: 58 percent / DPPA, NaHCO₃ / dimethylformamide / 72 h / 0 °C

14: diethyl ether / 0 °C

With hydrogenchloride; lithium hydroxide; borane-THF; copper(I) bromide dimethylsulfide complex; 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; nitrobenzene; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)93447-1

upstream raw materials:

diazomethane

Methyl (9S,12S,15S)-12-(2-amino-2-oxoethyl)-9-<<(phenylmethoxy)carbonyl>amino>-4-hydroxy-10,13-dioxo-2-oxa-11,14-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-15-carboxylate

dihydroisoferulic acid

(S)-2-amino-3-(4-chloro-phenyl)-propionic acid methyl ester hydrochloride

Downstream raw materials:

OF4949-III

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