Hydrochloric Acid → (4R)-3-(3-Bromopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid

HRID 68000

Reaction equation

HRID 68000 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[NH:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9]1.C(=O)([O-])[O-].[Na+].[Na+].[Br:22][CH2:23][CH2:24][C:25](Cl)=[O:26].Cl>O>[Br:22][CH2:23][CH2:24][C:25]([N:12]1[C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9][CH:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 84944Propanoyl chloride, 3-bromo-HCID 2825745(4R)-2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid

Product 1

HCID 54005883(4R)-3-(3-Bromopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 22.5 g of (4R)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid and 21.2 g of sodium carbonate in 200 ml of water, cooled by an ice-water bath, 18.8 g of 3-bromopropanoyl chloride is added dropwise. The resulting mixture is continuously stirred for 2 hr at room temperature, acidified with 2 N aqueous hydrochloric acid solution, and extracted with 300 ml of ethyl acetate. The organic layer is washed with brine and dried over sodium sulfate. After removal of ethyl acetate in vacuo, 100 ml of chloroform is added to the residue and the separated crystals are filtered to give 24.3 g (70%) of the product. The product is recrystallized from methanol to yield the titled compound: mp 109°-115° C.; IR (nujol) 3330, 1709, 1629, 1594, 1229, 1198, 1029 cm-1.

Workup

  1. extractionextracted with 300 ml of ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of ethyl acetate in vacuo, 100 ml of chloroform
  5. additionis added to the residue
  6. filtrationthe separated crystals are filtered

Sources & evidence

ORD record
ord-ef381c3cbed0465abc76a146f954a889
Source dataset
uspto-grants-1982_08
Patent number
US04347371

Linked notes

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