Sodium Hydroxide → HCID 20633663, compound

HRID 48373Notes

Reaction equation

HRID 48373 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])=[CH:4][CH:3]=1.[C:22]1([CH2:28][O:29][C:30]([NH:32][CH2:33][CH:34]=C)=[O:31])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.B1C2CCCC1CCC2.[OH-].[Na+]>Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].OO>[C:16]1([CH2:15][O:14][C:12]([NH:11][CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([CH2:34][CH2:33][NH:32][C:30]([O:29][CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:31])=[CH:3][CH:4]=2)=[O:13])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 562279Benzyl allylcarbamateHCID 22743235benzyl N-[3-(4-bromophenyl)propyl]carbamate

Product 1

HCID 20633663HCID 20633663, compoundYield 35.4%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 784Hydrogen PeroxideSolvent

Procedure

N-[3-(4-Bromophenyl)propyl](phenylmethoxy)carboxamide (1.5 g, 4.3 mmol), (phenylmethoxy)-N-eth-2-enylcarboxamide (0.92 g, 5.17 mmol, prepared in example 8), 9-BBN-dimer (0.84 g, 3.45 mmol), [1,1′bis(diphenylphosphino)-ferrocene] dichloropalladium (11), PdCl2(dppf), (0.175 9, 0.22 mmol), 3N sodium hydroxide (3 mL), and pH=7 buffer hydrogen peroxide (2:1, 10 mL) were combined in a manner analogous to the procedure described in example 6 to provide the intermediate title compound, (phenylmethoxy)-N-[3-(4-{2-[(phenylmethoxy)carbonylamino]ethyl}phenyl)propyl]carboxamide, (0.68 g, 35%). Electron spray M.S. 447 (M*+H).

Sources & evidence

ORD record
ord-562cb8c395cf4619985de4d69aac1107
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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