Fmoc-(2S,5S)-5-amino-1,2,4,5,6,7-hexahydroazepino[3,2,1-Hi]indole-4-one-2-carboxylic acid

Base Information

• Chemical Name: Fmoc-(2S,5S)-5-amino-1,2,4,5,6,7-hexahydroazepino[3,2,1-Hi]indole-4-one-2-carboxylic acid
• CAS No.: 204326-24-9
• Molecular Formula: C₂₈H₂₄N₂O₅
• Molecular Weight: 468.509
• DSSTox Substance ID: DTXSID10373297
• Nikkaji Number: J1.679.010I
• Mol file: 204326-24-9.mol

Synonyms:204326-24-9;Fmoc-(2S,5S)-5-amino-1,2,4,5,6,7-hexahydroazepino[3,2,1-Hi]indole-4-one-2-carboxylic acid;(2S,5S)-Fmoc-5-amino-1,2,4,5,6,7-hexahydro-azepino [3,2,1-HI] indole-4-one-2-carboxylic acid;(2S,11S)-11-(9H-fluoren-9-ylmethoxycarbonylamino)-12-oxo-1-azatricyclo[6.4.1.04,13]trideca-4,6,8(13)-triene-2-carboxylic acid;(3S,6S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-oxo-1,2,3,4,6,7-hexahydroazepino[3,2,1-hi]indole-6-carboxylic acid;Fmoc-Haic(2S,5S)-OH;SCHEMBL5917067;DTXSID10373297;MFCD00673792;AKOS025405491;AS-44166;CS-0120733;(2S)-4-Oxo-5beta-(9H-fluorene-9-ylmethoxycarbonylamino)-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2beta-carboxylic acid;(2S,5S)-5-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)-4-oxo-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-carboxylic acid;(2S,5S)-Fmoc-5-amino-1,2,4,5,6,7-hexahydro-azepino [3,2,1-hi] indole-4-one-2-carboxylic acid, AldrichCPR;(2S,5S)-Fmoc-5-amino-1,2,4,5,6,7-hexahydro-azepino[3,2,1-HI]indole-4-one-2-carboxylicacid;Azepino[3,2,1-hi]indole-2-carboxylicacid,1,2,4,5,6,7-hexahydro-5-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-oxo-,(2S,9S)-(9ci)

Chemical Property of Fmoc-(2S,5S)-5-amino-1,2,4,5,6,7-hexahydroazepino[3,2,1-Hi]indole-4-one-2-carboxylic acid

Chemical Property:

• PSA: 99.43000
• LogP: 4.15180
• Storage Temp.: Store at 0-5°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 468.16852187
• Heavy Atom Count: 35
• Complexity: 825

Purity/Quality:

99% ^*data from raw suppliers

(2S,5S)-Fmoc-5-amino-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indole-4-one-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C3C(=CC=C2)CC(N3C(=O)C1NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46)C(=O)O
• Isomeric SMILES: C1CC2=C3C(=CC=C2)C[C@H](N3C(=O)[C@H]1NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46)C(=O)O
• Uses: (2S,5S)-Fmoc-5-amino-1,2,4,5,6,7-hexahydro-azepino [3,2,1-hi] indole-4-one-2-carboxylic Acid is used in preparation of Phosphopeptide inhibitors of STAT3.

Technology Process of Fmoc-(2S,5S)-5-amino-1,2,4,5,6,7-hexahydroazepino[3,2,1-Hi]indole-4-one-2-carboxylic acid

There total 2 articles about Fmoc-(2S,5S)-5-amino-1,2,4,5,6,7-hexahydroazepino[3,2,1-Hi]indole-4-one-2-carboxylic acid 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: 56.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + 4,7-dioxo-5-(R)-(2,2,2-trifluoroacetylamino)-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-(S)-carboxylic acid methyl ester (160726-07-8) → Fmoc-(5-[(R)-amino]-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-4-one-2-(S)-carboxylate) (1147126-36-0,204326-24-9)

Guidance literature:

4,7-dioxo-5-(R)-(2,2,2-trifluoroacetylamino)-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-(S)-carboxylic acid methyl ester; With palladium 10% on activated carbon; hydrogen; In acetic acid; at 20 ℃; for 24h; under 2585.81 Torr;

With lithium hydroxide; In tetrahydrofuran; water; for 2h;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; In 1,4-dioxane; water; for 20h;

DOI:10.1021/jm801491w

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2S,5S)-4,7-dioxo-5-(2,2,2-trifluoroacetylamino)-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-carboxylic acid methyl ester (160798-17-4) → (2S,11S)-11-([[(9H-fluoren-9-yl)methoxy]carbonyl]amino)-12-oxo-1-azatricyclo[6.4.1.0^[4,13]]trideca-4(13),5,7-triene-2-carboxylic acid (204326-24-9)

Guidance literature:

(2S,5S)-4,7-dioxo-5-(2,2,2-trifluoroacetylamino)-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-carboxylic acid methyl ester; With palladium 10% on activated carbon; hydrogen;

With lithium hydroxide;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide;

DOI:10.1021/jm801491w

Reference yield: 91.0%

tert-butyl N-[3-[4-([[(2R,3S)-3-amino-5-carbamoylpentan-2-yl]oxy]methyl)phenyl]propyl]carbamate + (2S,11S)-11-([[(9H-fluoren-9-yl)methoxy]carbonyl]amino)-12-oxo-1-azatricyclo[6.4.1.0^[4,13]]trideca-4(13),5,7-triene-2-carboxylic acid (204326-24-9) → (9H-fluoren-9-yl)methyl N-[(2S,11S)-2-[[(3S,4R)-4-[[4-(3-[[(tert-butoxy)carbonyl]amino]propyl)phenyl]methoxy]-1-carbamoylpentan-3-yl]carbamoyl]-12-oxo-1-azatricyclo[6.4.1.0^[4,13]]trideca-4(13),5,7-trien-11-yl]carbamate

Guidance literature:

(2S,11S)-11-([[(9H-fluoren-9-yl)methoxy]carbonyl]amino)-12-oxo-1-azatricyclo[6.4.1.0^[4,13]]trideca-4⁽¹³⁾,5,7-triene-2-carboxylic acid; With triethylamine; HATU; In N,N-dimethyl acetamide; at 20 ℃; for 0.166667h; Inert atmosphere;

tert-butyl N-[3-[4-([[(2R,3S)-3-amino-5-carbamoylpentan-2-yl]oxy]methyl)phenyl]propyl]carbamate; In N,N-dimethyl acetamide; at 20 ℃; for 1h; Inert atmosphere;

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

4,7-dioxo-5-(R)-(2,2,2-trifluoroacetylamino)-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-(S)-carboxylic acid methyl ester

(2S,5S)-4,7-dioxo-5-(2,2,2-trifluoroacetylamino)-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-carboxylic acid methyl ester

Downstream raw materials:

C₂₆H₂₉N₄O₉P

C₂₈H₃₃N₄O₈P

C₂₉H₃₃F₂N₄O₇P

pβMCinn-Haic-Gln-NHBn

Refernces