Water → HCID 23399177, compound

HRID 1062356Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([S:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=3)=[CH:22][C:21]=2[Cl:34])[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][CH:49]=1)[CH2:45]Br.O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([S:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH2:45][C:44]4[CH:47]=[CH:48][CH:49]=[C:42]([Cl:41])[CH:43]=4)[CH:28]=3)=[CH:22][C:21]=2[Cl:34])[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of the compound of Example 34 (500 mg) in DMF (10 mL), potassium carbonate (500 mg) and m-chlorobenzyl bromide (0.16 mL) were added and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was then poured into water and was extracted with ethyl acetate. The organic phase was sequentially washed with water and a saturated aqueous solution of sodium chloride and was dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain the desired product (520 mg) as a colorless powder.

Workup

extractionwas extracted with ethyl acetate
washThe organic phase was sequentially washed with water
dry with materiala saturated aqueous solution of sodium chloride and was dried with anhydrous sodium sulfate
customThe solvent was removed by distillation under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-1b283064f32f4f71aeb953fc54bebf9d
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960692B2

Reaction notes

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