4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 54023959, compound

HRID 1902557Notes

Reaction equation

HRID 1902557 reaction equation
[I-].CS[C:4]1[S:5][CH2:6][C@@H:7]2[CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N+:8]=12.[NH2:17][C:18]1[S:19][CH:20]=[C:21]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:22]=1>N1C=CC=CC=1>[CH2:27]([O:26][C:24]([CH2:23][C:21]1[N:22]=[C:18]([N:17]=[C:4]2[N:8]3[CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH2:16][C@H:7]3[CH2:6][S:5]2)[S:19][CH:20]=1)=[O:25])[CH3:28]

Participants

4

Reactant 2

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Product 1

HCID 54023959HCID 54023959, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (18.1 g) is added to a solution of ethyl (2-aminothiazol-4-yl)acetate (10 g) in pyridine (300 cc). After 48 hours at a temperature of the order of 20° C., the solution is concentrated to dryness under reduced pressure (25 mm Hg; 3.3. kPa) at 60° C. The residue is dissolved in a mixture of methylene chloride (200 cc) and N sodium hydroxide solution (100 cc). The organic phase is decanted off, washed with water (3×100 cc), dried over sodium sulphate and then concentrated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 40° C. The residue is recrystallised by dissolving it in boiling acetonitrile (100 cc) and then cooling. The crystals formed are filtered off, washed with acetonitrile (20 cc) and then with diethyl ether (20 cc) and dried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa) to yield (S)-3-[(4-ethoxycarbonylmethylthiazol-2-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (11.7 g), m.p.=105° C.

Workup

  1. concentrationthe solution is concentrated to dryness under reduced pressure (25 mm Hg; 3.3. kPa) at 60° C
  2. dissolutionThe residue is dissolved in a mixture of methylene chloride (200 cc) and N sodium hydroxide solution (100 cc)
  3. customThe organic phase is decanted off
  4. washwashed with water (3×100 cc)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 40° C
  7. customThe residue is recrystallised
  8. dissolutionby dissolving it
  9. temperaturecooling
  10. customThe crystals formed
  11. filtrationare filtered off
  12. washwashed with acetonitrile (20 cc)
  13. dry with materialwith diethyl ether (20 cc) and dried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-2793f9fc4c21480db7e3b36b801faf2d
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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