Hydrochloric Acid → HCID 14479198, compound

HRID 1905113Notes

Reaction equation

HRID 1905113 reaction equation
[C:1]1([CH:7]([O:14][C:15](=[O:33])[C@H:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:28])[CH3:27])=[C:21]([O:29][C:30](=[O:32])[CH3:31])[CH:20]=2)[O:17][NH2:18])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:34][C:35]1[S:36][CH:37]=[C:38]([C:40](=O)[C:41]([OH:43])=[O:42])[N:39]=1.O.Cl>CN(C)C=O>[NH2:34][C:35]1[S:36][CH:37]=[C:38](/[C:40](=[N:18]/[O:17][C@H:16]([C:15]([O:14][CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:33])[C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:28])[CH3:27])=[C:21]([O:29][C:30](=[O:32])[CH3:31])[CH:20]=2)/[C:41]([OH:43])=[O:42])[N:39]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 127833204-Thiazoleacetic acid, 2-amino-alpha-oxo-HCID 14050776HCID 14050776, compound

Product 1

HCID 14479198HCID 14479198, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of the product obtained in Step 4 (20.3 g) in dimethylformamide (60 ml) was added 2-(2-amino-4-thiazolyl)glyoxylic acid (7.8 g). The mixture was allowed to stand until it reached room temperature, and stirred overnight. The reaction mixture was then poured into ice-cooled water (400 ml), and the pH of the resulting mixture was adjusted to 2.0 with 1N hydrochloric acid. The mixture was extracted twice with ethyl acetate (500 ml). The combined organic layer was washed with brine (200 ml) and dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure and the residue was dissolved in a small amount of chloroform. This solution was added dropwise to ether. The formed crystals were collected by filtration and washed with ether, giving 22.3 g of the objective compound as pale yellow crystals.

Workup

  1. customreached room temperature
  2. additionThe reaction mixture was then poured into ice-
  3. extractionThe mixture was extracted twice with ethyl acetate (500 ml)
  4. washThe combined organic layer was washed with brine (200 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe dried solution was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in a small amount of chloroform
  8. additionThis solution was added dropwise to ether
  9. filtrationThe formed crystals were collected by filtration
  10. washwashed with ether

Sources & evidence

ORD record
ord-6a0c51a328904fcd868d122ad32273b9
Source dataset
uspto-grants-1989_06
Patent number
US04840945

Reaction notes

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