Pyridine → HCID 86756586, compound

HRID 322893Notes

Reaction equation

HRID 322893 reaction equation
[CH:1]([C:3]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)=[CH:19][C:4]=1[O:5][CH:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:2].Cl.[CH2:31]([O:38][NH2:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.N1C=CC=CC=1>C(O)C>[OH2:2].[CH2:31]([O:38][N:39]=[CH:1][C:3]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)=[CH:19][C:4]=1[O:5][CH:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 102312Benzyloxyamine hydrochlorideHCID 22010348HCID 22010348, compound

Product 1

HCID 86756586HCID 86756586, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (RS)-4-[2-formyl-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoic acid (0.7 g), O-benzylhydroxylamine hydrochloride (0.48 g) and pyridine (1 mL) in ethanol (50 mL) is heated at 65° C. for 5 hours. The reaction mixture is evaporated. The residue is dissolved dichloromethane (80 mL), washed with 1 N hydrochloric acid, then with water, dried over magnesium sulphate and evaporated. The resulting oil is purified by flash chromatography on silica eluting with a mixture of dichloromethane and methanol (95:5 v/v). Fractions homogeneous in the required product are combined, evaporated and the solid residue triturated with pentane to give (RS)-4-[2-(benzyloxyiminomethyl)-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoic acid hydrate (0.2 g) as a cream coloured solid, m.p. 35-37° C. [Elemental analysis:- C,69.2; H,5.60; N,2.58; S,6.26%. Calculated for C25H23NO8.0.3H2O: - C,69.2; H,5.72; N,2.69; S,6.16%]

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionThe residue is dissolved dichloromethane (80 mL)
  3. washwashed with 1 N hydrochloric acid
  4. dry with materialwith water, dried over magnesium sulphate
  5. customevaporated
  6. customThe resulting oil is purified by flash chromatography on silica eluting with a mixture of dichloromethane and methanol (95:5 v/v)
  7. customevaporated
  8. customthe solid residue triturated with pentane

Sources & evidence

ORD record
ord-f84c4f4d33ec4852bab9ffdfedd3a296
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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