Dimethylformamide → HCID 14306189, compound

HRID 868316Notes

Reaction equation

HRID 868316 reaction equation
C([CH:3]1[CH2:11][N:10]2[C:5](=[CH:6][C:7]([CH:13]([O:19][C:20]([C@H:22]3[CH2:26][CH2:25][CH2:24][N:23]3[S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])=[O:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][C:9]2=[O:12])[C:4]21[O:40][CH2:39][CH2:38][O:37]2)#N.[H-].[Na+].[CH2:43](I)[CH3:44].[CH3:46][N:47](C)C=O>C(Cl)(Cl)Cl>[C:46]([C:8]1[C:9](=[O:12])[N:10]2[C:5](=[CH:6][C:7]=1[C@:13]([CH2:43][CH3:44])([O:19][C:20]([C@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[S:27]([C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)(=[O:28])=[O:29])=[O:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:4]1([O:37][CH2:38][CH2:39][O:40]1)[CH2:3][CH2:11]2)#[N:47]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 54466631HCID 54466631, compound

Product 1

HCID 14306189HCID 14306189, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolved in 28 ml of anhydrous N,N-dimethylformamide was 3.50 g of the compound (XII) obtained in the above procedure (2), followed by an addition of 248 mg of 60% NaH. After stirring the resultant mixture at room temperature for 1 hour, 5 ml of ethyl iodide was added and the resulting mixture was stirred at room temperature for 3 hours. After concentration of the reaction mixture under reduced pressure, the residue was dissolved in chloroform and the resulting chloroform solution was washed first with a 10% citric acid solution and then with water. The chloroform solution was dried over anhydrous sodium sulfate and then concentrated. The residue was subjected to column chromatography on silica gel and then developed with a 3:1 mixed solvent of benzene and ethyl acetate. A fraction containing the intended product was concentrated. The residue was crystallized from 2-propanol to obtain 2.07 g of the title compound.

Workup

  1. customobtained in the above procedure (2)
  2. washthe resulting chloroform solution was washed first with a 10% citric acid solution
  3. dry with materialThe chloroform solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionA fraction containing the intended product
  6. concentrationwas concentrated
  7. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-973d96853e9242dea523afb9250ef468
Source dataset
uspto-grants-1988_10
Patent number
US04778891

Reaction notes

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