(R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester

Base Information

Chemical Name:(R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester
CAS No.:275805-33-9
Molecular Formula:C₂₈H₄₁IN₄O₇
Molecular Weight:672.561
Hs Code.:

(R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester

Synonyms:(R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester

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Chemical Property of (R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester

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Technology Process of (R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester

There total 9 articles about (R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl 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:

: 100-83-4
meta-hydroxybenzaldehyde

: 275805-33-9
(R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / DBU / CH₂Cl₂ / 16 h / 25 °C

2: 90 percent / H₂ / [(S,S)-Et-DuP-Rh]⁺TfO^- / methanol / 96 h / 3102.97 Torr

3: 96 percent / H₂ / Pd/C / methanol / 12 h / 25 °C / 760.05 Torr

4: 78 percent / EDC; HOAt / CH₂Cl₂ / 3 h / 20 °C

5: 89 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 0 °C

6: 181 mg / HOAt; iPr₂NEt; EDC / CH₂Cl₂ / 4 h / 0 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; 1: Condensation / 2: stereoselective hydrogenation / 3: Hydrogenolysis / 4: Acylation / 5: Hydrolysis / 6: Condensation;
DOI:10.1021/ja994285v

Reference yield:

: 234122-64-6
(S)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)propanoate

: 275805-33-9
(R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / H₂ / Pd/C / methanol / 12 h / 25 °C / 760.05 Torr

2: 78 percent / EDC; HOAt / CH₂Cl₂ / 3 h / 20 °C

3: 89 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 0 °C

4: 181 mg / HOAt; iPr₂NEt; EDC / CH₂Cl₂ / 4 h / 0 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1: Hydrogenolysis / 2: Acylation / 3: Hydrolysis / 4: Condensation;
DOI:10.1021/ja994285v

Reference yield:

: 234122-56-6
(Z)-methyl 2-((benzyloxycarbonyl)amino)-3-(3-hydroxyphenyl)acrylate

: 275805-33-9
(R)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (E)-4-iodo-but-3-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / H₂ / [(S,S)-Et-DuP-Rh]⁺TfO^- / methanol / 96 h / 3102.97 Torr

2: 96 percent / H₂ / Pd/C / methanol / 12 h / 25 °C / 760.05 Torr

3: 78 percent / EDC; HOAt / CH₂Cl₂ / 3 h / 20 °C

4: 89 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 0 °C

5: 181 mg / HOAt; iPr₂NEt; EDC / CH₂Cl₂ / 4 h / 0 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; 1: stereoselective hydrogenation / 2: Hydrogenolysis / 3: Acylation / 4: Hydrolysis / 5: Condensation;
DOI:10.1021/ja994285v