1-(N-tert-Butyloxycarbonyl)glycyloxymethyl-5-fluorouracil

Base Information

• Chemical Name: 1-(N-tert-Butyloxycarbonyl)glycyloxymethyl-5-fluorouracil
• CAS No.: 149439-92-9
• Molecular Formula: C₁₂H₁₆FN₃O₆
• Molecular Weight: 317.274
• DSSTox Substance ID: DTXSID70164269
• Wikidata: Q83033326
• Mol file: 149439-92-9.mol

Synonyms:1-(N-tert-Butyloxycarbonyl)glycyloxymethyl-5-fluorouracil;149439-92-9;Glycine, N-((1,1-dimethylethoxy)carbonyl)-, (5-fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)methyl ester;(5-fluoro-2,4-dioxopyrimidin-1-yl)methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate;SCHEMBL17278256;C12H16FN3O6;DTXSID70164269;YBMMLOWXLDQBNN-UHFFFAOYSA-N;C12-H16-F-N3-O6;LS-72559

Chemical Property of 1-(N-tert-Butyloxycarbonyl)glycyloxymethyl-5-fluorouracil

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 123.24000
• Density: 1.38g/cm³
• LogP: 0.31780
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 317.10231340
• Heavy Atom Count: 22
• Complexity: 525

Purity/Quality:

1-(N-TERT-BUTYLOXYCARBONYL)GLYCYLOXYMETHYL-5-FLUOROURACIL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCC(=O)OCN1C=C(C(=O)NC1=O)F

Technology Process of 1-(N-tert-Butyloxycarbonyl)glycyloxymethyl-5-fluorouracil

There total 2 articles about 1-(N-tert-Butyloxycarbonyl)glycyloxymethyl-5-fluorouracil 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: 67.0%

BOC-glycine (4530-20-5) + 5-fluoro-1-(hydroxymethyl) pyrimidine-2,4-(1H,3H)-dione → (5-fluoro-2,4-dioxo-3,4-dihydropyrimidinyl-1-(2H))methyl-2-((tert-butoxycarbonyl)amino)acetate (149439-92-9)

Guidance literature:

BOC-glycine; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 0.5h; Cooling with ice;

5-fluoro-1-(hydroxymethyl) pyrimidine-2,4-(1H,3H)-dione; With trimethylamine; In dichloromethane; acetonitrile; for 20h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (5-fluoro-2,4-dioxo-3,4-dihydropyrimidinyl-1-(2H))methyl-2-((tert-butoxycarbonyl)amino)acetate (149439-92-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / tetrahydrofuran / pH 10 / Cooling with ice

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / Cooling with ice

2.2: 20 h

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; dichloromethane;

Reference yield:

(5-fluoro-2,4-dioxo-3,4-dihydropyrimidinyl-1-(2H))methyl-2-((tert-butoxycarbonyl)amino)acetate (149439-92-9) → (5-fluoro-2,4-dioxo-3,4-dihydropyrimidinyl-1(2H))methyl-2-((S)-2-((2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanamido)acetate hydrochloride

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.5 h / Cooling with ice

2.2: 5 h / 20 °C

3.1: hydrogenchloride / ethyl acetate / 2 h / 20 °C

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; ethyl acetate;

upstream raw materials:

di-tert-butyl dicarbonate

BOC-glycine

Refernces

• 1、 -. "DRUG FORMULATIONS FOR CANCER TREATMENT". Page/Page column 46; 47. . Retrieved 2017/07/27.