Dichloromethane → HCID 10093089, compound

HRID 1354518Notes

Reaction equation

HRID 1354518 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][NH:6][CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:2].[C:18]([CH2:21][N:22]1[CH:30]=[C:28]([CH3:29])[C:26](=[O:27])[NH:25][C:23]1=[O:24])(O)=[O:19].C(Cl)Cl.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]([CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:18](=[O:19])[CH2:21][N:22]1[CH:30]=[C:28]([CH3:29])[C:26](=[O:27])[NH:25][C:23]1=[O:24])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 4319362Ethyl N-{2-[(tert-butoxycarbonyl)amino]ethyl}glycinate

Product 1

HCID 10093089HCID 10093089, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

N-(N-Boc-2-aminoethyl)glycine ethyl ester (8, 13.5 g; 54.8 mmol), DhbtOH (9.84 g; 30 60.3 mmol) and N-1-carboxymethyl thymine (4, 11.1 g; 60.3 mmol) were dissolved in DMF (210 ml). Methylene chloride (210 ml) then was added. The solution was cooled to 0° C. in an ethanol/ice bath and DCC (13.6 g; 65.8 mmol) was added. The ice bath was removed after 1 hour and stirring was continued for another 2 hours at ambient temperature. The precipitated DCU was removed by filtration and washed twice with methylene chloride 5 (2×75 ml). To the combined filtrate was added more methylene chloride (650 ml). The solution was washed successively with diluted sodium hydrogen carbonate (3×500 ml), diluted potassium hydrogen sulfate (2×500 ml), and saturated sodium chloride (1×500 ml). Some precipitate was removed from the organic phase by filtration, The organic phase was dried over magnesium sulfate and evaporated to dryness, in vacuo. The oily residue was dissolved in methylene chloride (150 ml), filtered and the title compound was precipitated by the addition of petroleum ether (350 ml) at 0° C. The methylene chloride/petroleum ether procedure was repeated once. This afforded 16.0 g (71%) of the title compound which was more than 99% pure by HPLC.

Workup

  1. customThe ice bath was removed after 1 hour
  2. customThe precipitated DCU was removed by filtration
  3. washwashed twice with methylene chloride 5 (2×75 ml)
  4. additionTo the combined filtrate was added more methylene chloride (650 ml)
  5. washThe solution was washed successively with diluted sodium hydrogen carbonate (3×500 ml), diluted potassium hydrogen sulfate (2×500 ml), and saturated sodium chloride (1×500 ml)
  6. customSome precipitate was removed from the organic phase by filtration
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. customevaporated to dryness, in vacuo
  9. dissolutionThe oily residue was dissolved in methylene chloride (150 ml)
  10. filtrationfiltered
  11. customthe title compound was precipitated by the addition of petroleum ether (350 ml) at 0° C

Sources & evidence

ORD record
ord-5077c467983449e59022e98d6b25bf5a
Source dataset
uspto-grants-2007_05
Patent number
US07223833B1

Reaction notes

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