Water → HCID 66758529, compound

HRID 242551Notes

Reaction equation

HRID 242551 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:38])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[O:21][C:20]4[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH2:33][C:34](=[NH:37])[NH:35]O)[C:19]=4[CH2:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:39](N1C=CN=C1)(N1C=CN=C1)=[S:40].O.C(OCC)(=[O:54])C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:38])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[O:21][C:20]4[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH2:33][CH:34]5[NH:37][C:39](=[O:54])[S:40][NH:35]5)[C:19]=4[CH2:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 802641,1'-ThiocarbonyldiimidazoleHCID 178511388HCID 178511388, compound

Product 1

HCID 66758529HCID 66758529, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 407 (700 mg) in THF (20 ml) was added thiocarbonyldiimidazole (280 mg) and the mixture was stirred at room temperature for 30 minutes. Water and ethyl acetate were added to the reaction mixture. The organic layer was extracted, and the solvent was distilled off under reduced pressure. To the residue were added THF (50 ml) and boron trifluoride diethyl etherate (0.8 ml), and the mixture was stirred at room temperature for 1 hour. Chloroform, 2-propanol and water were added to the reaction mixture. The organic layer was extracted, and the solvent was distilled off under reduced pressure. The residue was reslurried with acetone to the titled compound (180 mg).

Workup

  1. extractionThe organic layer was extracted
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the residue were added THF (50 ml) and boron trifluoride diethyl etherate (0.8 ml)
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. additionChloroform, 2-propanol and water were added to the reaction mixture
  6. extractionThe organic layer was extracted
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-70f9808aa9f54a6e902d17e6b6cebb4f
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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