Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1709022Notes

Reaction equation

HRID 1709022 reaction equation
C([O:5]C(NCC(O)=O)=O)(C)(C)C.[CH:13]1([N:19]=[C:20]=[N:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(#N)C>[C:20]([NH:19][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)([NH:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:5]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 9.45 g of N-(t-butoxycarbonyl)-glycine in 60 ml of acetonitrile was added 6.13 g of dicyclohexylcarbodiimide with stirring under ice-cooling. After three hours, dicyclohexylurea produced was filtered off, and the filtrate was concentrated. The oily residue was dissolved in 15 ml of anhydrous pyridine, and to the solution was added 5.00 g of 3'-O-(4-chlorobenzyl)-2'-deoxy-5-fluorouridine. The mixture was left to stand for three hours at room temperature and for 30 minutes at a temperature of 40° C. To the mixture was added 5 ml of water at room temperature and the mixture was left to stand for 30 minutes and then concentrated. The residue was dissolved in 50 ml of ethyl acetate, and the solution was washed three times with saturated aqueous solution of sodium hydrogen carbonate and twice with saturated aqueous solution of sodium chloride. Further the solution was dried over anhydrous magnesium sulfate and concentrated. The residue was placed on silica gel column and eluted with 1% methanol-chloroform, giving 5.33 g (75%) of 5'-O-[N-(t-butoxycarbonyl)glycyl]-3'-O-(4-chlorobenzyl)-2'-deoxy-5-fluorouridine.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-7a2a753fe71843eabf8b3ee942a9921b
Source dataset
uspto-grants-1990_08
Patent number
US04946951

Reaction notes

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