Ethyl Glycolate → HCID 23634374, compound

HRID 2355066Notes

Reaction equation

HRID 2355066 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:14][CH2:13][C@H:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])[CH2:11]2)=[N:7][CH:6]=1)[NH2:4].[C:26](OCC)(=O)[CH2:27][OH:28].[O-]CC.[Na+]>C(O)C.O>[F:23][C:22]([F:25])([F:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][C@H:12]1[CH2:13][CH2:14][N:10]([C:8]2[S:9][C:5]([C:3]3[N:4]=[C:26]([CH2:27][OH:28])[O:1][N:2]=3)=[CH:6][N:7]=2)[CH2:11]1

Participants

6

Reactant 3

HCID 12184Ethyl GlycolateHCID 2723922Sodium ethoxideHCID 86629249HCID 86629249, compound

Product 1

HCID 23634374HCID 23634374, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of N′-hydroxy-2-{(3S)-3-[2-(trifluoromethyl)phenoxy]-pyrrolidin-1-yl}-1,3-thiazole-5-carboximidamide (373 mg, 1 mmol), ethyl glycolate (380 μL, 4 mmol) and sodium ethoxide, (21 wt. % solution in ethyl alcohol, 1.6 mL, 4.2 mmol) in ethanol (10 mL) was refluxed for 30 min. After cooling to rt, the mixture was diluted with water and extracted with EtOAc. The EtOAc extract was washed with water, dried (Na2SO4) and concentrated. The residue was triturated with Et2O to give the title compound as a pale yellow powder. 1H NMR (500 MHz, acetone-d6): δ 7.83 (s, 1 H), 7.69-7.65 (m, 2 H), 7.41 (d, 1 H), 7.16 (t, 1 H), 5.52 (m, 1 H), 5.05 (s, 1 H), 4.87 (s, 2 H), 3.98 (m, 1 H), 3.85-3.69 (m, 3 H), 2.60-2.44 (m, 2 H).

Workup

  1. temperaturewas refluxed for 30 min
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-75b1c87637854ea39060a9728e7e7449
Source dataset
uspto-grants-2010_07
Patent number
US07754745B2

Reaction notes

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