N-(1S,2R-N,O-dimethylacetonide-indanyl)-2R-(3-benzyloxy-phenylmethyl)-3-(tert-butoxycarbonyl)propanamide

Base Information

• Chemical Name: N-(1S,2R-N,O-dimethylacetonide-indanyl)-2R-(3-benzyloxy-phenylmethyl)-3-(tert-butoxycarbonyl)propanamide
• CAS No.: 220682-45-1
• Molecular Formula: C₃₄H₃₉NO₅
• Molecular Weight: 541.687
• Mol file: 220682-45-1.mol

Synonyms:N-(1S,2R-N,O-dimethylacetonide-indanyl)-2R-(3-benzyloxy-phenylmethyl)-3-(tert-butoxycarbonyl)propanamide

Chemical Property of N-(1S,2R-N,O-dimethylacetonide-indanyl)-2R-(3-benzyloxy-phenylmethyl)-3-(tert-butoxycarbonyl)propanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(1S,2R-N,O-dimethylacetonide-indanyl)-2R-(3-benzyloxy-phenylmethyl)-3-(tert-butoxycarbonyl)propanamide

There total 3 articles about N-(1S,2R-N,O-dimethylacetonide-indanyl)-2R-(3-benzyloxy-phenylmethyl)-3-(tert-butoxycarbonyl)propanamide 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: 61.0%

bromoacetic acid tert-butyl ester (5292-43-3) + N-(1S,2R-N,O-dimethylacetonide-indanyl)-3-(3-benzyloxy-phenyl)-propanamide (147008-23-9) → N-(1S,2R-N,O-dimethylacetonide-indanyl)-2R-(3-benzyloxy-phenylmethyl)-3-(tert-butoxycarbonyl)propanamide (220682-45-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 4h;

DOI:10.1021/jm015533c

Reference yield:

3-(3-(benzyloxy)phenyl)propanoic acid (57668-34-5) → N-(1S,2R-N,O-dimethylacetonide-indanyl)-2R-(3-benzyloxy-phenylmethyl)-3-(tert-butoxycarbonyl)propanamide (220682-45-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / BOP; diethylisopropyl amine / dimethylformamide / 5 h / 0 - 20 °C

2: 91 percent / PPTS / CH₂Cl₂ / 0 - 20 °C / cooling

3: 61 percent / LDA / tetrahydrofuran / 4 h / -78 °C

With N,N-diethyl-N-isopropylamine; pyridinium p-toluenesulfonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm015533c

Reference yield:

N-(1S,2R-indanyl-2-ol)-3-(3-benzyloxy-phenyl)-propanamide (374938-41-7) → N-(1S,2R-N,O-dimethylacetonide-indanyl)-2R-(3-benzyloxy-phenylmethyl)-3-(tert-butoxycarbonyl)propanamide (220682-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / PPTS / CH₂Cl₂ / 0 - 20 °C / cooling

2: 61 percent / LDA / tetrahydrofuran / 4 h / -78 °C

With pyridinium p-toluenesulfonate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm015533c

upstream raw materials:

bromoacetic acid tert-butyl ester

N-(1S,2R-N,O-dimethylacetonide-indanyl)-3-(3-benzyloxy-phenyl)-propanamide

3-(3-(benzyloxy)phenyl)propanoic acid

N-(1S,2R-indanyl-2-ol)-3-(3-benzyloxy-phenyl)-propanamide

Downstream raw materials:

3-biphenyl-4-ylmethyl-4-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-4-oxo-butyric acid tert-butyl ester