Methanol → HCID 21557715, compound

HRID 1579061Notes

Reaction equation

HRID 1579061 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:26])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[N:18][S:19][C:20]=2[C:21]([O:23]CC)=[O:22])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+]>O>[C:1]([NH:5][CH2:6][CH:7]([OH:26])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[N:18][S:19][C:20]=2[C:21]([OH:23])=[O:22])=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21557720HCID 21557720, compound

Product 1

HCID 21557715HCID 21557715, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 200 mg. of 4-[4(3-t-butylamino-2-hydroxypropoxy)phenyl]-5-carboethoxy-1,2,3-thiadiazole in 15 ml. of methanol is added a solution of 100 mg. of sodium hydroxide in 2 ml. of water, and the reaction mixture is refluxed for 4 hours. It is then cooled, evaporated to a small volume under vacuo, diluted with 25 ml. of water and extracted with ethyl acetate to eliminate the unsaponified product. The aqueous phase is passed through a column of 10 g. of ion exchange resin sold by the Dow Chemical Company under the trademark Dowex 50, acidic type (H+) eluting the column first with water and thereafter with 10% acetic acid solution. The combined acidic eluates are concentrated to a small volume under reduced pressure at low temperature and then lyophilized, to yield 4-[4(3-t-butylamino-2-hydroxypropoxy)phenyl]-5-carboxy-1,2,3-thiadiazole.

Workup

  1. temperatureIt is then cooled
  2. customevaporated to a small volume under vacuo
  3. additiondiluted with 25 ml
  4. extractionof water and extracted with ethyl acetate
  5. washeluting the column first with water
  6. concentrationThe combined acidic eluates are concentrated to a small volume under reduced pressure at low temperature

Sources & evidence

ORD record
ord-86a37ed0649f46a2804fc433dd694049
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

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