Methanol → HCID 19996087, compound

HRID 2248404Notes

Reaction equation

HRID 2248404 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:30])[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][C:21]2[S:25][C:24]([C:26]([O:28]C)=[O:27])=[CH:23][CH:22]=2)=[CH:4][C:3]=1[Cl:31].[OH-].[Na+].CO>CCCCCC>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:30])[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][C:21]2[S:25][C:24]([C:26]([OH:28])=[O:27])=[CH:23][CH:22]=2)=[CH:4][C:3]=1[Cl:31]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19996066HCID 19996066, compound

Product 1

HCID 19996087HCID 19996087, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of methyl 5-[2-[[6-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]hexyl]oxy]ethyl]-2-thiophenecarboxylate (0.274 g) in a 2N sodium hydroxide solution (4.5 ml) and methanol (20 ml) was stirred at room temperature under nitrogen for 28 h. Dowex 50 (H+) methanol-washed ion exchange resin was added portionwise to neutralise the mixture to pH7. The mixture was filtered and evaporated in vacuo to give an orange solid. Trituration with hexane gave the title compound as a yellow solid (229 mg), m.p. 178°-185° (decomp).

Workup

  1. washDowex 50 (H+) methanol-washed ion exchange resin
  2. additionwas added portionwise
  3. filtrationThe mixture was filtered
  4. customevaporated in vacuo
  5. customto give an orange solid

Sources & evidence

ORD record
ord-dce50a3707db4f068f6c14b26546ef40
Source dataset
uspto-grants-1991_08
Patent number
US05039697

Reaction notes

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