(S)-2-phthalimido-6-methyl-6-azidoheptanoic acid, phenylmethyl ester

Base Information

• Chemical Name: (S)-2-phthalimido-6-methyl-6-azidoheptanoic acid, phenylmethyl ester
• CAS No.: 197902-93-5
• Molecular Formula: C₂₃H₂₄N₄O₄
• Molecular Weight: 420.468
• Mol file: 197902-93-5.mol

Synonyms:(S)-2-phthalimido-6-methyl-6-azidoheptanoic acid, phenylmethyl ester

Chemical Property of (S)-2-phthalimido-6-methyl-6-azidoheptanoic acid, phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-phthalimido-6-methyl-6-azidoheptanoic acid, phenylmethyl ester

There total 7 articles about (S)-2-phthalimido-6-methyl-6-azidoheptanoic acid, phenylmethyl 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: 81.3%

(S)-2-phthalimido-6-methyl-6-hydroxyheptanoic acid, phenylmethyl ester (197902-92-4) → (S)-2-phthalimido-6-methyl-6-azidoheptanoic acid, phenylmethyl ester (197902-93-5)

Guidance literature:

With trimethylsilylazide; boron trifluoride diethyl etherate; In dichloromethane; for 120h; Ambient temperature;

DOI:10.1021/jm980542f

Reference yield:

benzyl bromide (100-39-0) → (S)-2-phthalimido-6-methyl-6-azidoheptanoic acid, phenylmethyl ester (197902-93-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / Cs₂CO₃ / dimethylformamide / 2 h / Ambient temperature

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 5 min

3: CH₂Cl₂ / 0.5 h

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -78 deg C to 0 deg C

5: 1.) TiCl₄ / 1.) Et₂O, from -78 deg C to -35 deg C, 2.) Et₂O, 0 deg C, 4 h

6: 81 percent / azidotrimethylsilane, BF₃*OEt₂ / CH₂Cl₂ / 120 h / Ambient temperature

With oxalyl dichloride; trimethylsilylazide; boron trifluoride diethyl etherate; titanium tetrachloride; caesium carbonate; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm980542f

Reference yield:

(S)-2-(1,3-dioxoisoindolin-2-yl)-6-hydroxyhexanoic acid (84688-11-9) → (S)-2-phthalimido-6-methyl-6-azidoheptanoic acid, phenylmethyl ester (197902-93-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / Cs₂CO₃ / dimethylformamide / 2 h / Ambient temperature

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 5 min

3: CH₂Cl₂ / 0.5 h

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -78 deg C to 0 deg C

5: 1.) TiCl₄ / 1.) Et₂O, from -78 deg C to -35 deg C, 2.) Et₂O, 0 deg C, 4 h

6: 81 percent / azidotrimethylsilane, BF₃*OEt₂ / CH₂Cl₂ / 120 h / Ambient temperature

With oxalyl dichloride; trimethylsilylazide; boron trifluoride diethyl etherate; titanium tetrachloride; caesium carbonate; dimethyl sulfoxide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm980542f

upstream raw materials:

(S)-2-phthalimido-6-methyl-6-hydroxyheptanoic acid, phenylmethyl ester

benzyl bromide

(S)-2-(1,3-dioxoisoindolin-2-yl)-6-hydroxyhexanoic acid

benzyl (S)-2-(1,3-dioxoisoindolin-2-yl)-6-oxohexanoate

Downstream raw materials:

(S)-Hexahydro-6-[(triphenylmethyl)amino]-2,2-dimethyl-7-oxo-1H-azepine-1-acetic acid, ethyl ester

[S-(R*,R*)]-Hexahydro-6-[[2-(acetylthio)-1-oxo-3-phenylpropyl]amino]-2,2-dimethyl-7-oxo-1H-azepine-1-acetic acid, ethyl ester

[14C]-Gemopatrilat

(S)-hexahydro-7,7-dimethyl-3-<(triphenylmethyl)amino>-2H-azepin-2-one