Water → HCID 70913777, compound

HRID 1844749Notes

Reaction equation

HRID 1844749 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]=3)=[CH:11][C:10]([S:27]([NH2:30])(=[O:29])=[O:28])=[C:9]2[CH3:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37].O>CN(C=O)C>[CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:22])([CH3:20])[CH3:21])[CH:16]=[C:15]([C:23]([CH3:24])([CH3:25])[CH3:26])[CH:14]=3)=[CH:11][C:10]([S:27]([NH:30][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])(=[O:29])=[O:28])=[C:9]2[CH3:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 66554786HCID 66554786, compound

Product 1

HCID 70913777HCID 70913777, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 1 (600 mg, 1.36 mmol) in dry DMF (10 mL) was added NaH (60%, 60 mg, 1.50 mmol) at 0° C. and the mixture was stirred at 0° C. for 10 min. Ethyl 2-bromoacetate (225 mg, 1.36 mmol) was added and then this mixture was stirred at rt for 5 h. Water was added for quench and the solution was extracted with EA. The organic layer was washed with brine twice, concentrated and purified by CC (PE/EA=5/1) to give compound 42 (150 mg, 21%) as a white solid.

Workup

  1. stirringthis mixture was stirred at rt for 5 h
  2. customfor quench
  3. extractionthe solution was extracted with EA
  4. washThe organic layer was washed with brine twice
  5. concentrationconcentrated
  6. custompurified by CC (PE/EA=5/1)

Sources & evidence

ORD record
ord-7883e45a0eab432aa4ddd12aa75896f8
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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