2-Bromopropane → HCID 9935036, compound

HRID 1741139Notes

Reaction equation

HRID 1741139 reaction equation
Br[CH:2]([CH3:4])[CH3:3].[NH2:5][C:6](=[O:37])[C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:18][CH2:19][C:20]([OH:22])=[O:21])[N:11]([CH2:23][C:24]2[CH:25]=[C:26]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]=[CH:28][CH:29]=2)[C:10]=1[CH3:36])=[O:8].[Na].C([O-])(O)=O.[Na+]>CN(C)C=O>[CH:2]([O:22][C:20](=[O:21])[CH2:19][O:18][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[C:9]([C:7](=[O:8])[C:6]([NH2:5])=[O:37])=[C:10]([CH3:36])[N:11]2[CH2:23][C:24]1[CH:25]=[C:26]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:27]=[CH:28][CH:29]=1)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 9955004HCID 9955004, compound

Product 1

HCID 9935036HCID 9935036, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a flask containing 15 ml of dimethylformamide was added with stirring 0.11 ml of 2-bromopropane and 500 mg. of ((3-(2-amino-1,2-dioxoethyl)-1-((1,1'-biphenyl)-3-ylmethyl)-2-methyl-1H-indol-4-yl)oxy)acetic acid, sodium salt. The reaction mixture was stirred at room temperature overnight. The reaction was incomplete. Thereafter, 180 mg of KI was added and the mixture was heated. After 24 hours the reaction mixture was poured into 50 ml of saturated NaHCO3 and extracted with ethyl acetate. The EtOAc solution was washed with water, dried over Na2SO4, and concentrated at reduced pressure. The title compound was then crystallized from EtOAc/hexane.

Workup

  1. additionwas added
  2. additionThereafter, 180 mg of KI was added
  3. temperaturethe mixture was heated
  4. extractionextracted with ethyl acetate
  5. washThe EtOAc solution was washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated at reduced pressure
  8. customThe title compound was then crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-88f00d5968844bf8a3ebb55d8e92fa01
Source dataset
uspto-grants-1999_10
Patent number
US05972988

Reaction notes

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