Water → HCID 131716364, compound

HRID 1649796Notes

Reaction equation

HRID 1649796 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:34])[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]2[C:27]([O:28][CH2:29][C:30]([O:32]C)=[O:31])=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:4][C:3]=1[Cl:35].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH2:42].[OH-].[Na+].CC[O:47][CH2:48][CH3:49]>>[C:48]([OH:47])(=[O:42])/[CH:49]=[CH:29]/[C:30]([OH:32])=[O:31].[NH2:1][C:2]1[C:3]([Cl:35])=[CH:4][C:5]([CH:9]([CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]2[C:27]([O:28][CH2:29][CH2:30][OH:31])=[CH:26][CH:25]=[CH:24][N:23]=2)[OH:34])=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 5

HCID 962Water2×HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54369192HCID 54369192, compound

Product 1

HCID 131716364HCID 131716364, compound

Procedure

Methyl [[2-[3-[[6-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]hexyl]oxy]propyl]-3-pyridinyl]oxy]acetate (400 mg) in ether (10 ml) was added dropwise to a stirred solution of lithium aluminum hydride (28 mg) in ether (5 ml) at 0° C. The mixture was stirred overnight at room temperature under nitrogen, water (0.5 ml) was added, followed by 2N sodium hydroxide (1.5 ml) and water (0.5 ml). The suspension was filtered through hyflo and washed with ethyl acetate (2×50 ml). Concentration of the filtrate gave an oil which was purified by FCC eluting with System A (95:5:1). The resulting oil (100 mg) was dissolved in methanol (2 ml) and treated with fumaric acid (12 mg). Concentration in vacuo gave an oil which was triturated several times under ether (3×10 ml) to give the title compound as a yellow solid (100 mg), m.p. 77°-80°.

Workup

  1. filtrationThe suspension was filtered through hyflo
  2. washwashed with ethyl acetate (2×50 ml)
  3. customConcentration of the filtrate gave an oil which
  4. customwas purified by FCC
  5. washeluting with System A (95:5:1)
  6. dissolutionThe resulting oil (100 mg) was dissolved in methanol (2 ml)
  7. additiontreated with fumaric acid (12 mg)
  8. concentrationConcentration in vacuo
  9. customgave an oil which
  10. customwas triturated several times under ether (3×10 ml)

Sources & evidence

ORD record
ord-02d1361a1d4646ab9aff98046fefea0a
Source dataset
uspto-grants-1990_05
Patent number
US04921867

Reaction notes

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