Water → HCID 178448114, compound

HRID 1419799Notes

Reaction equation

HRID 1419799 reaction equation
C(N(S(F)(F)F)CC)C.[Cl:10][C:11]1[C:12]([NH:19][C@H:20]2[CH2:25][CH2:24][C@@H:23]([C:26](O)([CH3:28])[CH3:27])[CH2:22][CH2:21]2)=[N:13][CH:14]=[N:15][C:16]=1[CH2:17][CH3:18].O>ClCCl>[Cl:10][C:11]1[C:12]([NH:19][C@H:20]2[CH2:25][CH2:24][C@@H:23]([C:26]([CH3:28])=[CH2:27])[CH2:22][CH2:21]2)=[N:13][CH:14]=[N:15][C:16]=1[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 178437731HCID 178437731, compound

Product 1

HCID 178448114HCID 178448114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.8 g (11 mmol) of diethylaminosulfur trifluoride (DAST) were added to 3.0 g (10 mmol) of the alcohol from Example 1 in 50 ml of dichloromethane at -50° C., and the mixture was stirred at room temperature for 1 hour. It was poured into water and the organic phase was washed with aqueous sodium hydrogen carbonate solution, dried and concentrated. The crude product was chromatographed on silica gel with petroleum ether/ethyl acetate 7:3 to give, first of all, 0.8 g (28.6% of theory) of the product indicated above as a colorless oil, and then 1.5 g (50.5% of theory) of the fluorination product described in Example 6, as a colorless oil (see Example 6).

Workup

  1. washthe organic phase was washed with aqueous sodium hydrogen carbonate solution
  2. customdried
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel with petroleum ether/ethyl acetate 7:3
  5. customto give

Sources & evidence

ORD record
ord-74b17e1afc7c426d9ea2e0795d60f8cf
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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