Dicyclohexylcarbodiimide → HCID 21868441, compound

HRID 2218589Notes

Reaction equation

HRID 2218589 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][NH:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)(=[O:12])=[O:11])[CH3:2].[N:23]1([CH2:32][C:33](O)=[O:34])[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]1=[O:25].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)(=[O:12])=[O:11])[C:33](=[O:34])[CH2:32][N:23]1[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]1=[O:25])[CH3:2]

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 21868443Ethyl 2-((2-(benzo[d]thiazole-2-sulfonamido)ethyl)amino)acetate

Product 1

HCID 21868441HCID 21868441, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of N-[2-(benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester (1.72 g, 5 mmol), (thymin-1-yl)-acetic acid (0.92 g, 5 mmol), HOBt (0.81 g, 6 mmol), and DCC (1.24 g, 6 mmol) in DMF (15 mL) was added N,N-diisopropylethylamine (1.31 mL, 7.5 mmol) at ambient temperature. The resulting reaction mixture was stirred for 5 h at the same temperature and the solvent was removed in vacuo to 5 mL. The residue was dissolved in dichloromethane (50 mL) and the precipitate was filtered. The filtrate was washed with 1N HCl aqueous solution, saturated sodium bicarbonate solution, and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated and the residue was triturated with ethyl alcohol. The resulting solid was filtered off and dried in vacuo to give the title compound (1.91 g, 75%) as a white solid. 1H NMR (500 MHz; DMSO-d6) δ 11.29 (s, 0.6H), 11.28 (s, 0.4H), 8.99 (brs, 0.6H), 8.82 (brs, 0.4H), 8.28 (m, 1H) 8.18 (d, 1H) 7.66 (m, 2H) 7.31 (s, 0.6H) 7.42 (s, 0.4H) 4.66 (s, 1.2H) 4.47 (s, 0.8H) 4.31 (s, 0.8H), 4.05 (s, 1.2H), 4.04 (q, 1.2H), 3.55 (t, 1.2H), 3.40˜3.34 (m, 2.8H), 3.20 (t, 0.8H), 1.73 (s, 3H), 1.19 (t, 1.2H), 1.14 (t, 1.8H).

Workup

  1. customThe resulting reaction mixture
  2. customthe solvent was removed in vacuo to 5 mL
  3. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  4. filtrationthe precipitate was filtered
  5. washThe filtrate was washed with 1N HCl aqueous solution, saturated sodium bicarbonate solution, and brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe residue was triturated with ethyl alcohol
  10. filtrationThe resulting solid was filtered off
  11. customdried in vacuo

Sources & evidence

ORD record
ord-6e0d4b59a7704f22948f3038f5884d94
Source dataset
uspto-grants-2008_08
Patent number
US07411065B2

Reaction notes

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