Hydrogen Peroxide → HCID 9805414, compound

HRID 992239Notes

Reaction equation

HRID 992239 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([O:30][CH2:31][CH3:32])[C:27]([OH:29])=[O:28])=[CH:21][CH:20]=3)[C:4]=2[CH:3]=1.[OH:33]O>C(O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12](=[O:33])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([O:30][CH2:31][CH3:32])[C:27]([OH:29])=[O:28])=[CH:21][CH:20]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 18411697HCID 18411697, compound

Product 1

HCID 9805414HCID 9805414, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(4-(2-(2-chloro-phenothiazin-10-yl)-ethoxy)-phenyl)-2-ethoxy-propionic acid (122 mg; 0.26 mmol) in ethanol (1 ml) was stirred at 60° C. and hydrogen peroxide (30%; 0.15 ml) was added. The reaction mixture was stirred for 30 min. and allowed to go to room temperature. The reaction mixture was evaporated and residue dissolved in water (5 ml). The aqueous phase was acidified with 1N HCl to pH 2 and extracted with methylene chloride (2×25 ml). The combined extracts were dried and evaporated. After column chromatography using ethyl acetate:methanol (4:1) as eluent the title compound was isolated in 116 mg (92%) yield. 1H NMR (CDCl3) δ1.10 (t, 3H), 2.80-3.04 (m, 2H), 3.24-3.38 (m, 1H), 3.45-3.60 (m, 1H), 3.93 (m, 1H), 4.38 (t, 2H), 4.58 (t, 2H), 6.82 (d, 2H), 7.10-8.0 (m, 9H), 8.0-8.7 (br. s, 1H). Compound 7.

Workup

  1. customto go to room temperature
  2. customThe reaction mixture was evaporated
  3. dissolutionresidue dissolved in water (5 ml)
  4. extractionextracted with methylene chloride (2×25 ml)
  5. customThe combined extracts were dried
  6. customevaporated
  7. customwas isolated in 116 mg (92%)
  8. customyield

Sources & evidence

ORD record
ord-43a3b6176b8848d188af93f74716a3e3
Source dataset
uspto-grants-2002_10
Patent number
US06468996B1

Reaction notes

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