Dicyclohexylcarbodiimide → HCID 21106018, compound

HRID 1354528Notes

Reaction equation

HRID 1354528 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][NH:5][CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:9].[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].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]([CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH3:9])[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]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 19754001HCID 19754001, compound

Product 1

HCID 21106018HCID 21106018, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-[(N-Boc)(N-methyl)-2-aminoethyl]-glycine methyl ester (0.9 g, 0.0037 mol) and DHBT-OH (0.65 g, 0.004 mol) in CH2Cl2 10 ml was added N-1-carboxymethylthymine (0.74 g, 0.04 mol) dissolved in DMF (6 ml). The solution was cooled in an ice bath and DCC (0.905, 0.049 mol) was added. The reaction mixture was stirred for 1 hour and the ice bath was removed. The reaction mixture was left for 16 hours at room temperature. The reaction mixture was filtered and washed twice with 1N KHSO4 (15 ml) and three times with NaHCO3 (15 ml), brine (10 ml) and water (10 ml) and dried with Na2SO4. The product was purified by column chromatography on silica gel with CH2Cl2/MeOH 95:5 eluent. The yield of the title compound was 55%.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customthe ice bath was removed
  3. waitThe reaction mixture was left for 16 hours at room temperature
  4. filtrationThe reaction mixture was filtered
  5. washwashed twice with 1N KHSO4 (15 ml) and three times with NaHCO3 (15 ml), brine (10 ml) and water (10 ml)
  6. dry with materialdried with Na2SO4
  7. customThe product was purified by column chromatography on silica gel with CH2Cl2/MeOH 95:5 eluent

Sources & evidence

ORD record
ord-91c00bebb3114a949c22b468da955d90
Source dataset
uspto-grants-2007_05
Patent number
US07223833B1

Reaction notes

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