Aspirin → HCID 3362775, compound

HRID 1178049Notes

Reaction equation

HRID 1178049 reaction equation
CCN([CH:7]([CH3:9])C)C(C)C.[C:10]([O:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=O)(=[O:12])[CH3:11].CCN=C=NCCC[N:31]([CH3:33])C.C1C=CC2N([OH:43])N=NC=2C=1.CN([CH:47]=[O:48])C>O>[CH2:7]([O:43][C:47](=[O:48])[CH2:33][NH:31][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[O:13][C:10](=[O:12])[CH3:11])[CH3:9]

Participants

7

Reactant 5

HCID 2244AspirinHCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 3362775HCID 3362775, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DIPEA (0.288 mL, 1.67 mmol) was added dropwise to 2-acetoxy benzoic acid (100 mg, 0.56 mmol) in DMF (5 mL). EDCI (266 mg, 1.39 mmol) and HOBT (90 mg, 0.67 mmol) were added consecutively and after 10 mins, glycine ethyl ester. HCl (92 mg, 0.67 mmoles) was added. The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford (2-Acetoxy-benzoyl amino)-acetic acid ethyl ester in 97% yield. 1H NMR (DMSO-D6): δ 12.2 (s, 1H), 9.2 (t, 1H), 7.9 (dd, 1H), 7.4 (dt, 1H), 6.9 (d, 2H), 4.2 (q, 2H), 4.1 (d, 2H), 3.8 (d, 1H), 1.3 (t, 3H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4f002135e5f4ee687b8280c3a6c9012
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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