3-Thiazolidineacetic acid, 4-oxo-2-thioxo- → HCID 3010771, compound

HRID 2213578Notes

Reaction equation

HRID 2213578 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[N:4]([CH2:8][C:9]([OH:11])=[O:10])[C:2]1=[S:3].[C:12]1([C@H:18]([O:23][C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=2[O:32][CH2:33][C@H:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH3:35])[CH:27]=O)[C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[NH4+]>CN(C)C=O.C(OCC)(=O)C.CO>[C:12]1([C@H:18]([O:23][C:24]2[CH:25]=[C:26]([CH:27]=[C:7]3[S:1][C:2](=[S:3])[N:4]([CH2:8][C:9]([OH:11])=[O:10])[C:5]3=[O:6])[CH:29]=[CH:30][C:31]=2[O:32][CH2:33][C@H:34]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH3:35])[C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 517165Ammonium AcetateHCID 58697784HCID 58697784, compound

Product 1

HCID 3010771HCID 3010771, compoundYield 73.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of rhodanine-3-acetic acid (461 mg, 2.41 mmol, 1 eq), 3-[(S)-1-phenyl-2,2,2-trifluoroethoxy]-4-[(S)-2-phenylpropoxy]benzaldehyde (1.0 g, 2.41 mmol, 1 eq) and ammonium acetate (558 mg, 7.24 mmol, 3 eq) in N,N-dimethylformamide (10 mL) was heated to 90° C. and stirred for 15 min. It was then cooled to room temperature and diluted with ethyl acetate (100 mL). The organic solution was washed with 1M HCl (2×200 mL), and brine (200 mL), then dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel; elution with ethyl acetate followed by ethyl acetate:methanol (9:1) gave a yellow gum which was dissolved in methanol (5 mL) and added dropwise to stirred ice-cold water (100 mL). A fine suspension was obtained, which was freeze-dried over 3 days to give the product as a yellow powder (1.04 g, 73%) mp 73–80° C.: 1H NMR (d6 DMSO) δ 7.64 (s, 1H, C═C—H), 6.04 (q, 1H, J 6.4 Hz, CHCF3), 4.61 (s, 2H, CH2CO2H), 4.22 (m, 2H, OCH2CHCH3Ph), 3.26 (m, 1H, OCH2CHCH3Ph), 1.38 (d, 3H, J 7.2 Hz, OCH2CHCH3Ph) 19F NMR (d6 DMSO) −75.80. Anal. Found: C, 59.31; H, 4.42; N, 2.36; Calcd for C29H24F3NO5S2: C, 59.27; H, 4.12; N, 2.38.

Workup

  1. washThe organic solution was washed with 1M HCl (2×200 mL), and brine (200 mL)
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified by chromatography on silica gel
  5. washelution with ethyl acetate
  6. customgave a yellow gum which
  7. additionadded dropwise
  8. customA fine suspension was obtained
  9. customwhich was freeze-dried over 3 days

Sources & evidence

ORD record
ord-3f16eb2f3ad24ae796d77dcdf2ff1550
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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