(2R)-2-hydroxy-N-[(1S,4R,5R)-4-hydroxy-5-phthalimidocyclohex-1-yl]-2-phenylacetamide

Base Information

• Chemical Name: (2R)-2-hydroxy-N-[(1S,4R,5R)-4-hydroxy-5-phthalimidocyclohex-1-yl]-2-phenylacetamide
• CAS No.: 1310055-79-8
• Molecular Formula: C₂₂H₂₂N₂O₅
• Molecular Weight: 394.427
• Mol file: 1310055-79-8.mol

Synonyms:(2R)-2-hydroxy-N-[(1S,4R,5R)-4-hydroxy-5-phthalimidocyclohex-1-yl]-2-phenylacetamide

Chemical Property of (2R)-2-hydroxy-N-[(1S,4R,5R)-4-hydroxy-5-phthalimidocyclohex-1-yl]-2-phenylacetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-hydroxy-N-[(1S,4R,5R)-4-hydroxy-5-phthalimidocyclohex-1-yl]-2-phenylacetamide

There total 4 articles about (2R)-2-hydroxy-N-[(1S,4R,5R)-4-hydroxy-5-phthalimidocyclohex-1-yl]-2-phenylacetamide 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: 80.0%

(2R)-2-hydroxy-N-[(1R,4R,5R)-4-hydroxy-5-phthalimidocyclohex-2-en-1-yl]-2-phenylacetamide (1310055-77-6) → (2R)-2-hydroxy-N-[(1S,4R,5R)-4-hydroxy-5-phthalimidocyclohex-1-yl]-2-phenylacetamide (1310055-79-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; under 2070.21 Torr;

DOI:10.1055/s-0030-1258430

Reference yield:

3-[(R)-mandeloyl]-7-phthalimido-2-oxa-3-azabicyclo[2.2.2]oct-5-ene (1310055-73-2) → (2R)-2-hydroxy-N-[(1S,4R,5R)-4-hydroxy-5-phthalimidocyclohex-1-yl]-2-phenylacetamide (1310055-79-8)

Guidance literature:

Multi-step reaction with 2 steps

1: bis(cyclopentadienyl)titanium dichloride; zinc / tetrahydrofuran; methanol / -30 - -15 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / methanol / 2070.21 Torr

With bis(cyclopentadienyl)titanium dichloride; palladium 10% on activated carbon; hydrogen; zinc; In tetrahydrofuran; methanol;

DOI:10.1055/s-0030-1258430

Reference yield:

N-(cyclohexa-2,4-dienyl)phthalimide (1248421-70-6) → (2R)-2-hydroxy-N-[(1S,4R,5R)-4-hydroxy-5-phthalimidocyclohex-1-yl]-2-phenylacetamide (1310055-79-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium periodate / dichloromethane; water; N,N-dimethyl-formamide / Inert atmosphere

2: bis(cyclopentadienyl)titanium dichloride; zinc / tetrahydrofuran; methanol / -30 - -15 °C / Inert atmosphere

3: palladium 10% on activated carbon; hydrogen / methanol / 2070.21 Torr

With bis(cyclopentadienyl)titanium dichloride; sodium periodate; palladium 10% on activated carbon; hydrogen; zinc; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1055/s-0030-1258430

upstream raw materials:

3-[(R)-mandeloyl]-7-phthalimido-2-oxa-3-azabicyclo[2.2.2]oct-5-ene

N-(cyclohexa-2,4-dienyl)phthalimide

(2R)-2-hydroxy-N-[(1R,4R,5R)-4-hydroxy-5-phthalimidocyclohex-2-en-1-yl]-2-phenylacetamide

(2R)-(-)-2-hydroxy-2-phenylacetohydroxamic acid