Methanol → HCID 19996087, compound

HRID 359755Notes

Reaction equation

HRID 359755 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-c5fa9552a2d9409c8a99815817d298a5
Source dataset
uspto-grants-1991_03
Patent number
US05002966

Reaction notes

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