6-tert-Butoxy-3-[(9H-fluoren-9-yl)(methoxycarbonyl)amino]-6-oxohexanoic acid

Base Information

• Chemical Name: 6-tert-Butoxy-3-[(9H-fluoren-9-yl)(methoxycarbonyl)amino]-6-oxohexanoic acid
• CAS No.: 203854-49-3
• Molecular Formula: C25H29NO6
• Molecular Weight: 439.508
• DSSTox Substance ID: DTXSID10694070
• Mol file: 203854-49-3.mol

Synonyms:DTXSID10694070;4-(2-(5-Cholro-2-methoxybenzamido)Ethyl)benzenesulfonylchloride;6-tert-Butoxy-3-[(9H-fluoren-9-yl)(methoxycarbonyl)amino]-6-oxohexanoic acid

Chemical Property of 6-tert-Butoxy-3-[(9H-fluoren-9-yl)(methoxycarbonyl)amino]-6-oxohexanoic acid

Chemical Property:

• Vapor Pressure: 3.4E-17mmHg at 25°C
• Melting Point: 115-120℃
• Refractive Index: 1.566
• Boiling Point: 638.8 °C at 760 mmHg
• PKA: 4.31±0.10(Predicted)
• Flash Point: 340.2 °C
• PSA: 101.93000
• Density: 1.214 g/cm³
• LogP: 4.88120
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 439.19948764
• Heavy Atom Count: 32
• Complexity: 664

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-L-beta-homoglutamic acid 6-tert-butyl ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CCC(CC(=O)O)N(C1C2=CC=CC=C2C3=CC=CC=C13)C(=O)OC
• Uses: N-Fmoc-L-beta-homoglutamic acid 6-tert-butyl ester is used as organic chemical synthesis intermediate.

Technology Process of 6-tert-Butoxy-3-[(9H-fluoren-9-yl)(methoxycarbonyl)amino]-6-oxohexanoic acid

There total 5 articles about 6-tert-Butoxy-3-[(9H-fluoren-9-yl)(methoxycarbonyl)amino]-6-oxohexanoic 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: 80.0%

Fmoc-Glu(OBut)-DAM (203854-39-1) → (3S)-3-([(9H-fluoren-9-yl)methoxy]carbonyl)aminohexanedioic acid 6-(tert-butyl) ester (203854-49-3)

Guidance literature:

With silver benzoate; In 1,4-dioxane; water; at 70 ℃; for 5h;

Reference yield:

Fmoc-Glu(OtBu)-OH (71989-18-9) → (3S)-3-([(9H-fluoren-9-yl)methoxy]carbonyl)aminohexanedioic acid 6-(tert-butyl) ester (203854-49-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / 1H-benzotriazol-1-yl-N-oxytris(NMe₂)phosphonium PF₆^(1-); N-ethyldiisopropylamine / tetrahydrofuran; dimethylformamide; diethyl ether / 0.25 h / 0 °C

2: 78 percent / silver benzoate / dioxane; H₂O / 70 °C

With silver benzoate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; N,N-dimethyl-formamide; 2: Wolff rearrangement;

Reference yield:

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-pentanedioic acid 5-tert-butyl ester; hydrate (204251-24-1) → (3S)-3-([(9H-fluoren-9-yl)methoxy]carbonyl)aminohexanedioic acid 6-(tert-butyl) ester (203854-49-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) i-BuOCOCl, NMM / 1.) THF, -20 deg C, 20 min, 2.) THF, Et₂O, -5 deg C, 4 h

2: 71 percent / CF₃COOAg, NMM / tetrahydrofuran; H₂O / 8 h

With 4-methyl-morpholine; silver trifluoroacetate; isobutyl chloroformate; In tetrahydrofuran; water;

DOI:10.1002/hlca.19980810202

upstream raw materials:

Fmoc-Glu(OBu^t)-DAM

Fmoc-Glu(OtBu)-OH

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-pentanedioic acid 5-tert-butyl ester; hydrate

Downstream raw materials:

H-β³hVal-β³hLys-β³hSer(All)-β³hPhe-β³hGlu-β³hSer(All)-β³hTyr-β³hIle-OH

C₇₃H₁₁₇N₉O₁₆

C₁₁₅H₁₆₁N₁₇O₂₇S₂

Refernces

• 1、 Vasanthakumar,Babu, V. V. Suresh. "Synthesis of Fmoc-/Boc-/Z-β-amino acids via Arndt-Eistert homologation of Fmoc-/Boc-/Z-α-amino acids employing BOP and PyBOP". . p. 1691 - 1695. Retrieved 2007/10/03.
• 2、 Ananda,Suresh Babu. "Convenient and simple synthesis of N-{[(9H-fluoren-9- yl)methoxy]carbonyl}-(Fmoc) protected β-amino acids (=homo-α-amino acids) employing Fmoc-α-amino acids and dicyclohexylcarbodiimide(DCC) mixtures". . p. 418 - 423. Retrieved 2007/10/03.