Ethanol → HCID 69899684, compound

HRID 351690Notes

Reaction equation

HRID 351690 reaction equation
[CH3:1][N:2]([CH2:19][C:20]([OH:22])=[O:21])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(N1C=CN=C1)(N1[CH:29]=[CH:28]N=C1)=O.C(O)C>O1CCCC1>[CH2:28]([O:21][C:20](=[O:22])[CH2:19][N:2]([CH3:1])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:13][CH2:14][C:15](=[O:18])[CH2:16][CH2:17]2)=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:29]

Participants

5

Reactant 3

HCID 702EthanolHCID 682631,1'-CarbonyldiimidazoleHCID 22713318HCID 22713318, compound

Product 1

HCID 69899684HCID 69899684, compoundYield 134%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.53 g (1.6 mmol) {methyl-[4-(4-oxo-piperidin-1-yl)-benzenesulfonyl]-amino}-acetic acid in 8 mL anhydrous tetrahydrofuran was treated with 0.32 g (2.0 mmol) 1,1′-carbonyl-diimidazole. After stirring for 45 minutes, 1 mL of ethanol was added. The resulting mixture was then permitted to stir overnight. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The organics were washed twice with saturated sodium bicarbonate, twice with water, dried over sodium sulfate and concentrated in vacuo. After drying via high vacuum overnight, 0.76 g of the title compound was isolated as a red solid; 1H NMR (CDCl3) δ 1.23-1.29 (m, 3H), 2.59 (t, J=6.15 Hz, 4H), 2.87 (s, 1H), 3.76 (t, J=6.09 Hz, 4H), 3.96 (s, 2H), 4.11-4.18 (m, 2H), 6.89-6.96 (m, 2H), 7.67-7.75 (m, 2H); MS (ES) m/z 355.3 (MH+); HRMS for C16H22N2O5S: 355.1332

Workup

  1. stirringto stir overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organics were washed twice with saturated sodium bicarbonate, twice with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customAfter drying via high vacuum overnight

Sources & evidence

ORD record
ord-61918aa578134b66b1bf04e922ac51db
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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