FMOC-D-CYCLOPROPYLGLYCINE

Base Information

• Chemical Name: FMOC-D-CYCLOPROPYLGLYCINE
• CAS No.: 923012-40-2
• Molecular Formula: C₂₀H₁₉NO₄
• Molecular Weight: 337.375
• Hs Code.: 29225090
• Mol file: 923012-40-2.mol

Synonyms:REF DUPL: Fmoc-D-Cyclopropylglycine;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-cyclopropylacetic acid;

Chemical Property of FMOC-D-CYCLOPROPYLGLYCINE

Chemical Property:

• Boiling Point: 577.1±33.0 °C(Predicted)
• PKA: 3.85±0.10(Predicted)
• PSA: 75.63000
• Density: 1.332±0.06 g/cm3(Predicted)
• LogP: 3.77920

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-D-cyclopropylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of FMOC-D-CYCLOPROPYLGLYCINE

There total 2 articles about FMOC-D-CYCLOPROPYLGLYCINE 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: 84.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (S)-2-amino-2-cyclopropylacetic acid (49606-99-7,5687-71-8,15785-26-9,49607-01-4) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid (1212257-18-5,1332765-55-5,923012-40-2)

Guidance literature:

(S)-2-amino-2-cyclopropylacetic acid; With sodium carbonate; In water; Inert atmosphere;

(fluorenylmethoxy)carbonyl chloride; In 1,4-dioxane; water; for 8h; Inert atmosphere;

DOI:10.1021/jacs.5b12557

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-2-amino-2-cyclopropylacetic acid (49606-99-7,5687-71-8,15785-26-9,49607-01-4) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid (1212257-18-5,1332765-55-5,923012-40-2)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 18h;

DOI:10.1002/anie.202017086

Reference yield:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopropylacetic acid (1212257-18-5,1332765-55-5,923012-40-2) → methyl (2S,4R)-4-(2-((1R,3R)-3-((S)-2-(3-acetamidobicyclo[1.1.1]pentane-1-carboxamido)-2-cyclopropyl-N-methylacetamido)-1-acetoxy-4-methylpentyl)thiazole-4-carboxamido)-2-methyl-5-phenylpentanoate

Guidance literature:

Multi-step reaction with 6 steps

1.1: diethylamino-sulfur trifluoride; pyridine / dichloromethane / 1 h / Inert atmosphere

2.1: 4-methyl-morpholine / N,N-dimethyl-formamide / 18 h / Inert atmosphere; Cooling with ice

3.1: 2,2',2''-triaminotriethylamine / dichloromethane / 3 h / Inert atmosphere; Cooling with ice

4.1: 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere

4.2: 24 h / Inert atmosphere

5.1: dichloromethane / 12 h / Inert atmosphere; Cooling with ice

6.1: pyridine / 6 h / Inert atmosphere; Cooling with ice

With 4-methyl-morpholine; pyridine; 1-hydroxy-7-aza-benzotriazole; 2,2',2''-triaminotriethylamine; diethylamino-sulfur trifluoride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jacs.5b12557

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(S)-2-amino-2-cyclopropylacetic acid

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