FMOC-3-ENDO-AMINOBICYCLO[2.2.1]HEPTANE-2-ENDO-CARBOXYLIC ACID

Base Information

• Chemical Name: FMOC-3-ENDO-AMINOBICYCLO[2.2.1]HEPTANE-2-ENDO-CARBOXYLIC ACID
• CAS No.: 917098-99-8
• Molecular Formula: C₂₃H₂₃NO₄
• Molecular Weight: 377.44
• Mol file: 917098-99-8.mol

Synonyms:(1R,2S,3R,4S)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}bicyclo[2.2.1]heptane-2-carboxylic acid;3-(endo-9-Fluorenylmethoxycarbonylamino)bicyclo[2.2.1]heptane-2-endo-carboxylic acid;

Chemical Property of FMOC-3-ENDO-AMINOBICYCLO[2.2.1]HEPTANE-2-ENDO-CARBOXYLIC ACID

Chemical Property:

• Vapor Pressure: 1.7E-15mmHg at 25°C
• Boiling Point: 605.2oC at 760 mmHg
• Flash Point: 319.8oC
• PSA: 75.63000
• Density: 1.34g/cm3
• LogP: 4.41530

Purity/Quality:

98%min ^*data from raw suppliers

3-(endo-9-Fluorenylmethoxycarbonylamino)bicyclo[2.2.1]heptane-2-endo-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of FMOC-3-ENDO-AMINOBICYCLO[2.2.1]HEPTANE-2-ENDO-CARBOXYLIC ACID

There total 4 articles about FMOC-3-ENDO-AMINOBICYCLO[2.2.1]HEPTANE-2-ENDO-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: 74.0%

(±)-cis-3-aminobicyclo[2.2.1]heptane-2-carboxylic acid hydrochloride (179462-36-3) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (±)-cis-3-(9-fluorenylmethyloxycarbonyl)aminobicyclo[2.2.1]heptane-2-carboxylic acid (352707-75-6,917098-99-8)

Guidance literature:

(±)-cis-3-aminobicyclo[2.2.1]heptane-2-carboxylic acid hydrochloride; With potassium hydrogencarbonate; In water; at 20 ℃;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; In water; acetonitrile; at 20 ℃;

DOI:10.1021/op010204f

Reference yield:

norbornene (498-66-8) → (±)-cis-3-(9-fluorenylmethyloxycarbonyl)aminobicyclo[2.2.1]heptane-2-carboxylic acid (352707-75-6,917098-99-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dichloromethane / 8 h / 0 - 25 °C

2.1: sodium sulfite; sodium hydroxide; water / 0 - 25 °C / pH 5 - 7

3.1: hydrogenchloride / water / Cooling with ice

4.1: potassium hydrogencarbonate / water / 20 °C

4.2: 20 °C

With hydrogenchloride; water; potassium hydrogencarbonate; sodium hydroxide; sodium sulfite; In dichloromethane; water;

DOI:10.1021/op010204f

Reference yield:

N-(Chlorosulfonyl)-exo-3-aza-4-ketotricyclo<4.2.1.02,5>nonane (14932-21-9) → (±)-cis-3-(9-fluorenylmethyloxycarbonyl)aminobicyclo[2.2.1]heptane-2-carboxylic acid (352707-75-6,917098-99-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium sulfite; sodium hydroxide; water / 0 - 25 °C / pH 5 - 7

2.1: hydrogenchloride / water / Cooling with ice

3.1: potassium hydrogencarbonate / water / 20 °C

3.2: 20 °C

With hydrogenchloride; water; potassium hydrogencarbonate; sodium hydroxide; sodium sulfite; In water;

DOI:10.1021/op010204f

upstream raw materials:

(±)-cis-3-aminobicyclo[2.2.1]heptane-2-carboxylic acid hydrochloride

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

norbornene

N-(Chlorosulfonyl)-exo-3-aza-4-ketotricyclo<4.2.1.0^2,5>nonane

Refernces

• 1、 Dener, Jeffrey M.,Fantauzzi, Pascal P.,Kshirsagar, Tushar A.,Kelly, Daphne E.,Wolfe, Aaron B.. "Large-scale syntheses of FMOC-protected non-proteogenic amino acids: Useful building blocks for combinatorial libraries". . p. 445 - 449. Retrieved 2013/09/07.