Sodium Chloride → HCID 66757963, compound

HRID 556933Notes

Reaction equation

HRID 556933 reaction equation
[C:1]([C:4]1[C:9]2[CH2:10][C:11](=[CH:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][C:25]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)([OH:28])[CH2:24][CH2:23]3)[C:12]3[C:13]([O:18][C:8]=2[CH:7]=[CH:6][CH:5]=1)=[N:14][CH:15]=[CH:16][CH:17]=3)(=[O:3])[CH3:2].[Li+].CC([N-]C(C)C)C.C([C:46]([O:48][CH2:49][CH3:50])=[O:47])#N.[Cl-].[NH4+].[Cl-].[Na+]>C1COCC1>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:25]2([OH:28])[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH:19]=[C:11]3[C:12]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=4)[O:18][C:8]4[CH:7]=[CH:6][CH:5]=[C:4]([C:1](=[O:3])[CH2:2][C:46]([O:48][CH2:49][CH3:50])=[O:47])[C:9]=4[CH2:10]3)[CH2:23][CH2:24]2)=[CH:34][CH:33]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 25517Ammonium ChlorideHCID 69336Ethyl cyanoformateHCID 2724682Lithium diisopropylamideHCID 66758417HCID 66758417, compound

Product 1

HCID 66757963HCID 66757963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 315 (250 mg) in THF (3.0 ml) was added LDA (0.51 mol/L THF-hexane solution, 3.0 ml) at −78° C., and the mixture stirred at room temperature for 20 minutes. The reaction mixture was cooled to −78° C. again, and added ethyl cyanoformate (76 μl), stirred at room temperature for 1 hour. Saturated aqueous ammonium chloride and aqueous sodium chloride were added to the mixture, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with chloroform-methanol (10:1) to give the titled compound (280 mg).

Workup

  1. temperatureThe reaction mixture was cooled to −78° C. again
  2. stirringstirred at room temperature for 1 hour
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with chloroform-methanol (10:1)

Sources & evidence

ORD record
ord-985ceea5352448baa75bddac92e97c6c
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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