Water → HCID 70869231, compound

HRID 1844728Notes

Reaction equation

HRID 1844728 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:12]2[N:16]([CH2:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:15]([CH3:24])=[C:14]([S:25]([NH2:28])(=[O:27])=[O:26])[CH:13]=2)[CH:8]=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40].O>CN(C=O)C>[C:1]([C:5]1[CH:10]=[C:9]([CH:8]=[C:7]([C:12]2[N:16]([CH2:17][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[C:15]([CH3:24])=[C:14]([S:25](=[O:27])(=[O:26])[NH2:28])[CH:13]=2)[CH:6]=1)[O:11][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 107604Methyl 4-bromobutyrateHCID 70869112HCID 70869112, compound

Product 1

HCID 70869231HCID 70869231, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of compound 14 (202 mg, 0.5 mmol) in DMF (20 mL) were added Cs2CO3 (325 mg, 1 mmol) and methyl 4-bromobutanoate (99 mg, 0.55 mmol). The reaction mixture was stirred for 4 h at 40° C., then water (30 mL) was added and the reaction mixture was extracted with EA (150 mL). The organic layer was washed with brine and dried over Na2SO4, concentrated and purified by CC (hexane/EA=3/1) to give compound 15 (176 mg, 70%).

Workup

  1. extractionthe reaction mixture was extracted with EA (150 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by CC (hexane/EA=3/1)

Sources & evidence

ORD record
ord-f06e853b10c940d9affb1780c5063a4f
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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