1-Bromoethyl acetate → HCID 15116516, compound

HRID 1886698Notes

Reaction equation

HRID 1886698 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:28]/[OH:29])/[C:8]([NH:10][C@@H:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([O-:25])=[O:24])=[C:15](/[CH:18]=[CH:19]\[CH:20]4[CH2:22][CH2:21]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:31]([O:34][CH:35](Br)[CH3:36])(=[O:33])[CH3:32]>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:28]/[OH:29])/[C:8]([NH:10][C@@H:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([O:25][CH:35]([O:34][C:31](=[O:33])[CH3:32])[CH3:36])=[O:24])=[C:15](/[CH:18]=[CH:19]\[CH:20]4[CH2:22][CH2:21]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 2

HCID 111375051-Bromoethyl acetateHCID 23700615HCID 23700615, compound

Product 1

HCID 15116516HCID 15116516, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The compound (318 mg) of Example 57 was dissolved in dimethylformamide (4.4 ml), to which a solution of 1-acetoxyethyl bromide (120 mg) in dimethylformamide (2 ml) was added dropwise under ice cooling. The resulting mixture was stirred for one and a half hours. The reaction mixture was diluted with ethyl acetate and the resulting precipitate was filtered off. After the filtrate was washed with water and then saturated saline, anhydrous magnesium sulfate was added to dry the solution. The solvent was distilled off under reduced pressure and the residue was purified by chromatography on a silica gel, whereby the title compound (18 mg) was obtained.

Workup

  1. additionwas added dropwise under ice cooling
  2. filtrationthe resulting precipitate was filtered off
  3. washAfter the filtrate was washed with water
  4. additionsaturated saline, anhydrous magnesium sulfate was added
  5. customto dry the solution
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by chromatography on a silica gel, whereby the title compound (18 mg)
  8. customwas obtained

Sources & evidence

ORD record
ord-41b8169104f64b33809bd3375d1219e2
Source dataset
uspto-grants-1992_09
Patent number
US05151417

Reaction notes

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