Thiazolidine → HCID 19894090, compound

HRID 892800Notes

Reaction equation

HRID 892800 reaction equation
C1(N=[C:8]=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)CCCCC1.[S:16]1[CH2:20][CH2:19][NH:18][CH2:17]1.NC1C=C(C=CC=1)[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26].[OH2:36].O[N:38]1[C:42]2C=[CH:44][CH:45]=[CH:46][C:41]=2N=N1>CN(C)C=O.O>[C:25]([C:14]1[CH:15]=[C:10]([NH:9][C:8]([CH:19]2[CH2:20][S:16][CH:17]([C:41]3[CH:42]=[N:38][CH:44]=[CH:45][CH:46]=3)[NH:18]2)=[O:36])[CH:11]=[CH:12][CH:13]=1)(=[O:26])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 10444ThiazolidineHCID 10868DicyclohexylcarbodiimideHCID 17817Methanone, (3-aminophenyl)phenyl-HCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 19894090HCID 19894090, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dicyclohexyl carbodiimide (DCC, 3.4 g, 16.7 mmole) was added to a solution of the thiazolidine acid prepared as described above in step 1 (2.3 g, 11 mmole), 3-aminobenzophenone (2.2 g, 11 mmole), and 1-hydroxybenzotriazole hydrate (HOBT, 1.5 g, 11 mmole) in dimethylformamide (25 mL). The reaction mixture was stirred for 20 hours at room temperature and then water (5 mL) was added to quench the excess DCC. Twenty minutes later ethylacetate was added and the mixture filtered to remove dicyclohexyl urea. The filtrate was washed with saturated sodium bicarbonate, water and saturated sodium chloride the dried over magnesium sulfate. The solvent was removed in vacuo and the residue chromatographed on 200 g silica gel eluting with 5% methanol in methylene chloride to yield the desired product (1.7 g, 40%). MS (DCI-NH3) m/e:386 (M+1)+ ; 1H NMR (CDCl3) d 3.43-3.62 (c, 1.5H), 3.82 (dd, 0.5H, J=4.5, 12), 4.20-4.30 (c, 0.5H), 4.54 (m, 0.5H, J=4.0), 4.98 (d, 0.5H, J=12), 5.72 (bs, 0.5H), 7.32-7.62 (c, 7H) 7.76-8.05 (c, 6H), 8.53 (dd, 0.5H, J=2,5), 8.62 (dd, 0.5H, J=2,5), 8.80 (b s, 0.5H), 9.28 (s, 0.5H).

Workup

  1. customprepared
  2. customto quench the excess DCC
  3. additionTwenty minutes later ethylacetate was added
  4. filtrationthe mixture filtered
  5. customto remove dicyclohexyl urea
  6. washThe filtrate was washed with saturated sodium bicarbonate, water and saturated sodium chloride the
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed in vacuo
  9. customthe residue chromatographed on 200 g silica gel eluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-2c567aa85cec4256bea62dd7830bd25f
Source dataset
uspto-grants-1992_06
Patent number
US05120751

Reaction notes

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