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

Base Information

• Chemical Name: 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
• CAS No.: 127559-23-3
• Molecular Formula: C₃₁H₃₂N₄O₉
• Molecular Weight: 604.616

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 18 articles about 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 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: 58.0%

(S)-3-(3-{4-[(S)-2-((S)-2-Amino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-hydroxy-phenyl)-2-benzyloxycarbonylamino-propionic acid; hydrochloride (127559-22-2) → 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)

Guidance literature:

With diphenyl-phosphinic acid; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 ℃; for 72h;

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

Reference yield:

N-<(Phenylmethoxy)carbonyl>-O-(phenylmethyl)-3-<4-(hydroxymethyl)phenoxy>-L-tyrosine 2-(trimethylsilyl)ethyl ester (127559-16-4) → 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)

Guidance literature:

Multi-step reaction with 9 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

With hydrogenchloride; carbon tetrabromide; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; N,N-dimethyl-formamide;

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

Reference yield:

N-<(Phenylmethoxy)carbonyl>-O-(phenylmethyl)-3-<4-(hydroxymethyl)phenoxy>-L-tyrosine (127559-15-3) → 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)

Guidance literature:

Multi-step reaction with 10 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

With hydrogenchloride; carbon tetrabromide; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

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

upstream raw materials:

(S)-3-(3-{4-[(S)-2-((S)-2-Amino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-hydroxy-phenyl)-2-benzyloxycarbonylamino-propionic acid; hydrochloride

sodium 4-iodo-benzoate

N-<(Phenylmethoxy)carbonyl>-O-(phenylmethyl)-3-<4-(hydroxymethyl)phenoxy>-L-tyrosine

N-<(Phenylmethoxy)carbonyl>-O-(phenylmethyl)-3-<4-(hydroxymethyl)phenoxy>-L-tyrosine methyl ester

Downstream raw materials:

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

(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-carboxylic acid

OF4949-IV

OF4949-III

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