5-Azaspiro[2.5]octane-6,7-dicarboxylic acid, 7-(1,1-dimethylethyl) ester, (6S,7S)-

Base Information

• Chemical Name: 5-Azaspiro[2.5]octane-6,7-dicarboxylic acid, 7-(1,1-dimethylethyl) ester, (6S,7S)-
• CAS No.: 791834-47-4
• Molecular Formula: C13H21NO4
• Molecular Weight: 255.314
• Mol file: 791834-47-4.mol

Synonyms:(6S,7S)-7-(tert-butoxycarbonyl)-5-azaspiro[2.5]octane-6-carboxylic acid;5-aza-spiro[2.5]octane-6,7-dicarboxylic acid 7-tert-butyl ester;

Chemical Property of 5-Azaspiro[2.5]octane-6,7-dicarboxylic acid, 7-(1,1-dimethylethyl) ester, (6S,7S)-

Chemical Property:

• PSA: 75.63000
• LogP: 1.49980

Purity/Quality:

99% ^*data from raw suppliers

(6S,7S)-7-(tert-butoxycarbonyl)-5-azaspiro[2.5]octane-6-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Azaspiro[2.5]octane-6,7-dicarboxylic acid, 7-(1,1-dimethylethyl) ester, (6S,7S)-

There total 8 articles about 5-Azaspiro[2.5]octane-6,7-dicarboxylic acid, 7-(1,1-dimethylethyl) ester, (6S,7S)- 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: 98.0%

5,6-dibenzyl 7-tert-butyl (6S,7S)-5-azaspiro[2.5]octane-5,6,7-tricarboxylate (791834-46-3) → (6S,7S)-7-(tert-butoxycarbonyl)-5-azaspiro[2,5]octane-6-carboxylic acid (791834-47-4)

Guidance literature:

With hydrogen; Pd-BaSO₄; In methanol; at 20 ℃; for 3h;

DOI:10.1021/jm061344o

Reference yield:

1,2-dibenzyl 3-tert-butyl (2S,3S)-5-methylenepiperidine-1,2,3-tricarboxylate (791834-45-2) → (6S,7S)-7-(tert-butoxycarbonyl)-5-azaspiro[2,5]octane-6-carboxylic acid (791834-47-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / palladium(II) acetate / diethyl ether / -20 - 20 °C

2: 98 percent / hydrogen / Pd/BaSO₄ / methanol / 3 h / 20 °C

With hydrogen; Pd-BaSO₄; palladium diacetate; In methanol; diethyl ether;

DOI:10.1055/s-2007-968029

Reference yield:

(S)-2-benzylamino-succinic acid 1-benzyl ester 4-tert-butyl ester (791834-41-8) → (6S,7S)-7-(tert-butoxycarbonyl)-5-azaspiro[2,5]octane-6-carboxylic acid (791834-47-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / K₂CO₃; NaI / acetonitrile / 16 h / 81 °C

2: 96 percent / NaI / acetone / 16 h / 20 °C

3: 72 percent / LiHMDS / tetrahydrofuran / 4 h / -78 - -30 °C

4: 93 percent / 28 h / 65 °C

5: 98 percent / palladium(II) acetate / diethyl ether / -20 - 20 °C

6: 98 percent / H₂ / Pd/BaSO₄ / methanol / 3 h / 20 °C

With hydrogen; potassium carbonate; sodium iodide; lithium hexamethyldisilazane; Pd-BaSO₄; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; acetone; acetonitrile;

DOI:10.1021/jm061344o

upstream raw materials:

5,6-dibenzyl 7-tert-butyl (6S,7S)-5-azaspiro[2.5]octane-5,6,7-tricarboxylate

1,2-dibenzyl 3-tert-butyl (2S,3S)-5-methylenepiperidine-1,2,3-tricarboxylate

(S)-2-benzylamino-succinic acid 1-benzyl ester 4-tert-butyl ester

2-benzyl 3-tert-butyl (2S,3S)-1-benzyl-5-methylenepiperidine-2,3-dicarboxylate

Downstream raw materials:

tert-butyl (6S,7S)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-7-carboxylate

tetrahydro-2H-pyran-4-yl (6S,7S)-7-((hydroxyamino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate

methyl (6S,7S)-7-[(hydroxyamino)carbonyl]-6-[(4-phenylpiperazin-1-yl)carbonyl]-5-azaspiro[2.5]octane-5-carboxylate

C₂₆H₃₆N₂O₃

Refernces

• 1、 Yao, Wenqing,Zhuo, Jincong,Burns, David M.,Xu, Meizhong,Zhang, Colin,Li, Yun-Long,Qian, Ding-Quan,He, Chunhong,Weng, Lingkai,Shi, Eric,Lin, Qiyan,Agrios, Costas,Burn, Timothy C.,Caulder, Eian,Covington, Maryanne B.,Fridman, Jordan S.,Friedman, Steven,Katiyar, Kamna,Hollis, Gregory,Li, Yanlong,Liu, Changnian,Liu, Xiangdong,Marando, Cindy A.,Newton, Robert,Pan, Max,Scherle, Peggy,Taylor, Nancy,Vaddi, Kris,Wasserman, Zelda R.,Wynn, Richard,Yeleswaram, Swamy,Jalluri, Ravi,Bower, Michael,Zhou, Bing-Bing,Metcalf, Brian. "Discovery of a potent, selective, and orally active human epidermal growth factor receptor-2 sheddase inhibitor for the treatment of cancer". . p. 603 - 606. Retrieved 2007/10/03.