Potassium Carbonate → HCID 118939063, compound

HRID 524022Notes

Reaction equation

HRID 524022 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH2:8][CH2:7][N:6]1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([NH:25][C:26](=[O:28])[CH3:27])[CH3:24])=[CH:19][CH:18]=1)=[O:4].Br[CH2:30][CH:31]1[CH2:33][CH2:32]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3]([CH:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:30][CH:31]3[CH2:33][CH2:32]3)=[CH:12][CH:13]=2)[CH2:8][CH2:7][N:6]1[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C@@H:23]([NH:25][C:26](=[O:28])[CH3:27])[CH3:24])=[CH:21][CH:22]=1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 118939112HCID 118939112, compound

Product 1

HCID 118939063HCID 118939063, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

15 mg (39 μmol) 2-[4-((S)-1-Acetylamino-ethyl)-benzyl]-6-hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid methyl ester (example XXXVIII), 5.8 mg (43 μmol) (bromomethyl)cyclopropane and 10 mg (78 μmol) K2CO3 in 2 mL DMF are stirred at 80° C. over night. The reaction mixture is diluted with water and extracted with DCM. The organic layer is concentrated by evaporation and the residue is purified by HPLC.

Workup

  1. extractionextracted with DCM
  2. concentrationThe organic layer is concentrated by evaporation
  3. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-ad3da40447ce4f43b1c1608daec400cf
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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