(3S)-1-{[3-(benzyloxycarbonyl)amino]-2-oxopiperidin-1-yl}-1-methylurea

Base Information

• Chemical Name: (3S)-1-{[3-(benzyloxycarbonyl)amino]-2-oxopiperidin-1-yl}-1-methylurea
• CAS No.: 1417900-17-4
• Molecular Formula: C₁₅H₂₀N₄O₄
• Molecular Weight: 320.348
• Mol file: 1417900-17-4.mol

Synonyms:

Chemical Property of (3S)-1-{[3-(benzyloxycarbonyl)amino]-2-oxopiperidin-1-yl}-1-methylurea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-1-{[3-(benzyloxycarbonyl)amino]-2-oxopiperidin-1-yl}-1-methylurea

There total 10 articles about (3S)-1-{[3-(benzyloxycarbonyl)amino]-2-oxopiperidin-1-yl}-1-methylurea 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:

(3S)-3-[(benzyloxycarbonyl)amino]-1-amino-piperidin-2-one (1417900-08-3) → (3S)-1-{[3-(benzyloxycarbonyl)amino]-2-oxopiperidin-1-yl}-1-methylurea (1417900-17-4)

Guidance literature:

Multi-step reaction with 4 steps

1: magnesium sulfate; acetic acid / tetrahydrofuran; water / 4 h / 20 °C

2: sodium cyanoborohydride / tetrahydrofuran; acetic acid / 0 - 20 °C

3: 1,4-dioxane / 1.5 h / Reflux

4: water

With water; sodium cyanoborohydride; magnesium sulfate; acetic acid; In tetrahydrofuran; 1,4-dioxane; water; acetic acid;

DOI:10.1021/ol3030583

Reference yield:

(3S)-3-[(benzyloxycarbonyl)amino]-1-(methylamino)piperidin-2-one (1417900-09-4) → (3S)-1-{[3-(benzyloxycarbonyl)amino]-2-oxopiperidin-1-yl}-1-methylurea (1417900-17-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,4-dioxane / 1.5 h / Reflux

2: water

With water; In 1,4-dioxane;

DOI:10.1021/ol3030583

Reference yield:

Cbz-L-Gln (2650-64-8) → (3S)-1-{[3-(benzyloxycarbonyl)amino]-2-oxopiperidin-1-yl}-1-methylurea (1417900-17-4)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 24 h / 20 °C

2: tert.-butylnitrite / acetonitrile / 1.5 h / Reflux

3: 4-methyl-morpholine / tetrahydrofuran / 0.08 h / 0 °C

4: sodium tetrahydroborate / methanol / 0.33 h / 0 °C

5: carbon tetrabromide; triphenylphosphine / dichloromethane / 2 h / 0 - 20 °C

6: hydrazine hydrate / methanol / 24.75 h / 20 °C

7: magnesium sulfate; acetic acid / tetrahydrofuran; water / 4 h / 20 °C

8: sodium cyanoborohydride / tetrahydrofuran; acetic acid / 0 - 20 °C

9: 1,4-dioxane / 1.5 h / Reflux

10: water

With 4-methyl-morpholine; sodium tetrahydroborate; tert.-butylnitrite; hydrazine hydrate; carbon tetrabromide; water; sodium cyanoborohydride; sodium hydrogencarbonate; magnesium sulfate; acetic acid; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol3030583

upstream raw materials:

(3S)-3-[(benzyloxycarbonyl)amino]-1-amino-piperidin-2-one

(3S)-3-[(benzyloxycarbonyl)amino]-1-(methylamino)piperidin-2-one

Cbz-L-Gln

N²-benzyloxycarbonyl-L-glutamine methyl ester

Refernces