Sodium Carbonate → HCID 86592150, compound

HRID 601334Notes

Reaction equation

HRID 601334 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:6]=1[NH:19][C:20](=O)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=[O:4])=[O:3].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:12]([O:11][C:9]1[CH:8]=[CH:7][C:6]2[NH:19][C:20]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:1][S:2](=[O:4])(=[O:3])[C:5]=2[CH:10]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 67063703Ethyl 3-{[2-(aminosulfonyl)-4-(benzyloxy)phenyl]amino}-3-oxopropanoate

Product 1

HCID 86592150HCID 86592150, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of Example 352A (292 mg, 0.744 mmol) and sodium carbonate (394 mg, 3.722 mmol) in anhydrous ethanol (12 mL) was heated to reflux under a nitrogen atmosphere for 6.5 hours. The reaction was cooled to room temperature, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with 3% methanol/dichloromethane to give the title compound as a white solid (237 mg, 85%). MS (ESI−) m/z 373 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ 1.21 (t, J=6.99 Hz, 3 H) 3.67 (s, 2 H) 4.16 (q, J=6.99 Hz, 2 H) 5.20 (s, 2 H) 7.39 (m, 8 H) 12.21 (s, 1 H).

Workup

  1. temperatureto reflux under a nitrogen atmosphere for 6.5 hours
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel eluting with 3% methanol/dichloromethane

Sources & evidence

ORD record
ord-faefa0d2d2574c1aba46c37dbd9f9c6f
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

Loading…