N-methyl-(R)-2-[(R)-2-(hydroxyamino)-1-(2-hydroxyacetylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide

Base Information

• Chemical Name: N-methyl-(R)-2-[(R)-2-(hydroxyamino)-1-(2-hydroxyacetylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide
• CAS No.: 1374429-31-8
• Molecular Formula: C₂₅H₃₂N₄O₆
• Molecular Weight: 484.552

Synonyms:N-methyl-(R)-2-[(R)-2-(hydroxyamino)-1-(2-hydroxyacetylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide

Chemical Property of N-methyl-(R)-2-[(R)-2-(hydroxyamino)-1-(2-hydroxyacetylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide

Chemical Property:

Purity/Quality:

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Technology Process of N-methyl-(R)-2-[(R)-2-(hydroxyamino)-1-(2-hydroxyacetylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide

There total 14 articles about N-methyl-(R)-2-[(R)-2-(hydroxyamino)-1-(2-hydroxyacetylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide 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: 84.0%

N-methyl-(R)-2-[(R)-2-(benzyloxyamino)-1-(2-hydroxyacetylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide (1374429-28-3) → N-methyl-(R)-2-[(R)-2-(hydroxyamino)-1-(2-hydroxyacetylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide (1374429-31-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/ejoc.201101318

Reference yield:

(E)-7-phenylhept-3-en-2-ol → N-methyl-(R)-2-[(R)-2-(hydroxyamino)-1-(2-hydroxyacetylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide (1374429-31-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: Novozym 435 / 18 h / 20 °C / Inert atmosphere; Enzymatic reaction

2.1: water; sodium hydroxide / methanol / 0 - 20 °C / Inert atmosphere

3.1: dmap; dicyclohexyl-carbodiimide / diethyl ether / 20 h / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium; diisopropylamine; zinc(II) chloride / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

5.1: caesium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

6.1: ozone / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

6.2: 0.5 h / -78 - 20 °C / Inert atmosphere

7.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 16 h / 20 °C / Inert atmosphere

8.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

10.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 0.33 h / -20 °C / Inert atmosphere

10.2: 20 °C / Inert atmosphere

11.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

12.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / N,N-dimethyl-formamide / 20 h / 0 - 20 °C / Inert atmosphere

13.1: palladium 10% on activated carbon; hydrogen / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With 4-methyl-morpholine; hydrogenchloride; dmap; sodium chlorite; n-butyllithium; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; Novozym 435; palladium 10% on activated carbon; water; hydrogen; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ozone; triethylamine; diisopropylamine; dicyclohexyl-carbodiimide; sodium hydroxide; zinc(II) chloride; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: Claisen rearrangement;

DOI:10.1002/ejoc.201101318

Reference yield:

(2R,E)-7-phenylhept-3-en-2-ol (1374429-38-5) → N-methyl-(R)-2-[(R)-2-(hydroxyamino)-1-(2-hydroxyacetylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide (1374429-31-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: dmap; dicyclohexyl-carbodiimide / diethyl ether / 20 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium; diisopropylamine; zinc(II) chloride / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

3.1: caesium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

4.1: ozone / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 - 20 °C / Inert atmosphere

5.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 16 h / 20 °C / Inert atmosphere

6.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

8.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 0.33 h / -20 °C / Inert atmosphere

8.2: 20 °C / Inert atmosphere

9.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

10.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / N,N-dimethyl-formamide / 20 h / 0 - 20 °C / Inert atmosphere

11.1: palladium 10% on activated carbon; hydrogen / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With 4-methyl-morpholine; hydrogenchloride; dmap; sodium chlorite; n-butyllithium; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; palladium 10% on activated carbon; hydrogen; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ozone; triethylamine; diisopropylamine; dicyclohexyl-carbodiimide; zinc(II) chloride; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Claisen rearrangement;

DOI:10.1002/ejoc.201101318

upstream raw materials:

(2R,E)-7-phenylhept-3-en-2-ol

(2R,E)-7-phenylhept-3-en-2-yl 2-(tert-butoxycarbonylamino)acetate

benzyl (2R,3S,E)-2-(tert-butoxycarbonylamino)-3-(3-phenylpropyl)hex-4-enoate

(R)-2-[(R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-oxoethyl]-5-phenylpentanoic acid

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