Dicyclohexylcarbodiimide → HCID 21092798, compound

HRID 1348972Notes

Reaction equation

HRID 1348972 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][NH:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[N:16][N:17]=1)(=[O:12])=[O:11])[CH3:2].O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[N:52]1([CH2:61][C:62](O)=[O:63])[CH:60]=[C:58]([CH3:59])[C:56](=[O:57])[NH:55][C:53]1=[O:54]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][N:6]([CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[N:16][N:17]=1)(=[O:12])=[O:11])[C:62](=[O:63])[CH2:61][N:52]1[CH:60]=[C:58]([CH3:59])[C:56](=[O:57])[NH:55][C:53]1=[O:54])[CH3:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 21092795HCID 21092795, compound

Product 1

HCID 21092798HCID 21092798, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of N-{2-[5-(4-Chlorophenyl)-1,3,4-thiadiazole-2-sulfonylamino]-ethyl}-glycine ethyl ester (4.05 g, 10 mmol) in 30 mL of DMF, were added 1.68 g (11 mmol) of 1-hydroxybenzotriazole monohydrate, 2.27 g (11 mmol) of dicyclohexylcarbodiimide and 1.84 g (10 mmol) of (thymin-1-yl)-acetic acid. The reaction mixture was stirred for 3 hours at room temperature. The precipitated dicyclohexylurea was filtered off and the filtrate was concentrated in vacuo, followed by column chromatography on silica gel to give the title compound (4.85 g, 8.5 mmol, 85%). 1H NMR (500 MHz; DMSO-d6) δ 11.28 (s, 0.6H), 11.26 (s, 0.4H), 9.15 (brs, 0.6H), 9.00 (brs, 0.4H), 8.07 (d, 2H), 7.67 (d, 2H), 7.31 (s, 0.6H), 7.24 (s, 0.4H), 4.65 (s, 1.2H), 4.47 (s, 0.8H), 4.31 (s, 0.8H), 4.16 (q, 0.8H), 4.06 (q, 1.2H), 4.03 (s, 1.2H), 3.55 (t, 1.2H), 3.45–3.38 (m, 2H), 3.23 (t, 0.8H), 1.73 (s, 3H), 1.21 (t, 1.2H), 1.16 (t, 1.8H).

Workup

  1. filtrationThe precipitated dicyclohexylurea was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-63910f0efd864c2d83c02fcdd5eda39e
Source dataset
uspto-grants-2007_05
Patent number
US07211668B2

Reaction notes

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