Tetrahydrofuran → HCID 19981691, compound

HRID 1460413Notes

Reaction equation

HRID 1460413 reaction equation
CO[S:3][C:4]([CH3:25])([CH3:24])[C@H:5]([C:21]([OH:23])=O)[N:6](CC1C=CC=CC=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH3:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.ON1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2N=N1.[CH:43]1(N=C=NC2CCCCC2)CCCCC1.[O:58]1CCC[CH2:59]1>>[C:10]([O:9][C:7]([NH:6][CH:5]([C:21]([N:30]1[CH2:31][CH2:32][CH:27]([CH3:26])[CH2:28][CH2:29]1)=[O:23])[C:4]([S:3][CH2:43][C:37]1[CH:42]=[CH:41][C:40]([O:58][CH3:59])=[CH:39][CH:38]=1)([CH3:24])[CH3:25])=[O:8])([CH3:11])([CH3:12])[CH3:13]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 10868DicyclohexylcarbodiimideHCID 693814-MethylpiperidineHCID 757711-HydroxybenzotriazoleHCID 22841629HCID 22841629, compound

Product 1

HCID 19981691HCID 19981691, compoundYield 100%

Procedure

To a solution of Compound (28) (29.6 g; 80.0 mmol) and 4-methylpiperidine (10.4 ml; 88.0 mmol) in tetrahydrofuran (100 ml), 1-hydroxybenzotriazole (16.2 g; 120 mmol) was added under cooling. Dicyclohexylcarbodiimide (18.2 g; 88.0 mmol) in tetrahydrofuran (50 ml) was dropwise added thereto, and the resultant mixture was stirred under cooling for 1 hour and at room temperature for 4 hours. After removal of insoluble materials by filtration, the filtrate was concentrated and combined with ethyl acetate. The resulting mixture was washed with 10% citric acid, a saturated aqueous sodium chloride solution, a saturated aqueous sodium hydrogen carbonate solution and a saturated sodium chloride solution in order three times. The organic layer was collected, dried over anhydrous sodium sulfate and concentrated to give Compound (29) (36.0 g; yield, 100%).

Workup

  1. temperatureunder cooling
  2. customAfter removal of insoluble materials
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated
  5. washThe resulting mixture was washed with 10% citric acid
  6. customThe organic layer was collected
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fd34a778a9534c88ad7f78723fd9d9a1
Source dataset
uspto-grants-1991_12
Patent number
US05071636

Reaction notes

Loading…