Thiazolidinedione → HCID 11257617, compound

HRID 1745403Notes

Reaction equation

HRID 1745403 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH2:14][O:13][CH:12]([CH2:17]O)[C:11]=2[S:10][C:9]=1[NH2:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:39]1[CH2:43][C:42](=[O:44])[NH:41][C:40]1=[O:45].CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH2:14][O:13][CH:12]([CH2:17][N:41]3[C:42](=[O:44])[CH2:43][S:39][C:40]3=[O:45])[C:11]=2[S:10][C:9]=1[NH2:19])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 5437ThiazolidinedioneHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 69585917HCID 69585917, compound

Product 1

HCID 11257617HCID 11257617, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-7-hydroxymethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (0.13 g, 0.46 mmol) in tetrahydrofuran (3 ml) was added triphenylphosphine (0.13 g, 0.51 mmol), and thiazolidin-2,4-dione (60 mg, 0.51 mmol). The reaction mixture was cooled to 0° C. and diisopropylazodicarboxylate (99 μl, 0.51 mmol) was added via syringe. The resultant mixture was stirred for 18 hours, gradually warming to room temperature. The volatiles were evaporated in vacuo and the resulting oil was diluted in ethyl acetate (50 ml). The organic phase was washed with saturated sodium bicarbonate (3×50 ml), brine (3×50 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was subjected to flash chromatography using a mixture of dichloromethane/methanol (9:1) as eluent. Pure fractions were collected (Rf=0.70) and the solvent evaporated in vacuo which afforded 89 mg (51%) of 2-amino-7-(2,4-dioxo-thiazolidin-3-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as an oil.

Workup

  1. temperaturegradually warming to room temperature
  2. customThe volatiles were evaporated in vacuo
  3. additionthe resulting oil was diluted in ethyl acetate (50 ml)
  4. washThe organic phase was washed with saturated sodium bicarbonate (3×50 ml), brine (3×50 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. additiona mixture of dichloromethane/methanol (9:1) as eluent
  9. customPure fractions were collected (Rf=0.70)
  10. customthe solvent evaporated in vacuo which

Sources & evidence

ORD record
ord-4e7f50171b814172b79b21a0d5f8f5c1
Source dataset
uspto-grants-2006_03
Patent number
US07019026B1

Reaction notes

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