Sodium Hydroxide → HCID 86743886, compound

HRID 1649795Notes

Reaction equation

HRID 1649795 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:33])[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[CH:23]=[C:24]([CH2:28][C:29](OC)=[O:30])[CH:25]=[N:26][CH:27]=2)=[CH:4][C:3]=1[Cl:34].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[C:43]([OH:50])(=[O:49])/[CH:44]=[CH:45]/[C:46]([OH:48])=[O:47]>C1C=CC=CC=1.CCOCC.CO.O>[C:43]([OH:50])(=[O:49])/[CH:44]=[CH:45]/[C:46]([OH:48])=[O:47].[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:33])[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[CH:23]=[C:24]([CH2:28][CH2:29][OH:30])[CH:25]=[N:26][CH:27]=2)=[CH:4][C:3]=1[Cl:34]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 21226445Aluminium lithium hydride2×HCID 53810510HCID 53810510, compound

Product 1

HCID 86743886HCID 86743886, compoundYield 156.1%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Methyl 5-[3-[[6-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]hexyl]oxy]propyl]-3-pyridineacetate (800 mg) in benzene (10 ml) was added dropwise to a stirred suspension of lithium aluminum hydride (95 mg) in ether (10 ml) at 0° C. The mixture was stirred overnight at room temperature under nitrogen, and more lithium aluminum hydride (40 mg) was added. After being stirred for a further 3 h, the mixture was treated with water (1 ml), followed by 2N sodium hydroxide (1 ml) and water (3 ml). The suspension was filtered through hyflo and washed with ethyl acetate (3×50 ml). The combined organic extracts were dried and concentrated to give a yellow oil which was purified by FCC eluting with System A (85:5:1) to give a yellow oil. The oil (450 mg), dissolved in methanol (10 ml), was treated with fumaric acid (52 mg) and concentrated to give an oil which was triturated with ether to give the title compound as a yellow solid (420 mg), m.p. 85°-86° C.

Workup

  1. stirringAfter being stirred for a further 3 h
  2. filtrationThe suspension was filtered through hyflo
  3. washwashed with ethyl acetate (3×50 ml)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customto give a yellow oil which
  7. customwas purified by FCC
  8. washeluting with System A (85:5:1)
  9. customto give a yellow oil
  10. concentrationconcentrated
  11. customto give an oil which
  12. customwas triturated with ether

Sources & evidence

ORD record
ord-6563ad0cff6b4c219eb9e0203de3f5ab
Source dataset
uspto-grants-1990_05
Patent number
US04921867

Reaction notes

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