4-(Benzyloxy)benzoic acid → HCID 67496802, compound

HRID 1920563Notes

Reaction equation

HRID 1920563 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[BrH:51].[Br-].[NH2:53][CH2:54][CH2:55][N+:56]12[CH2:63][CH2:62][CH:59]([CH2:60][CH2:61]1)[C@@H:58]([O:64][C:65](=[O:80])[C:66]([OH:79])([C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[CH2:57]2>CN(C=O)C>[Br-:51].[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:53][CH2:54][CH2:55][N+:56]23[CH2:63][CH2:62][CH:59]([CH2:60][CH2:61]2)[C@@H:58]([O:64][C:65](=[O:80])[C:66]([OH:79])([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[C:73]2[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=2)[CH2:57]3)=[O:15])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 738804-(Benzyloxy)benzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67496660HCID 67496660, compound

Product 1

HCID 67496802HCID 67496802, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-benzyloxybenzoic acid (0.126 mg, 0.55 mmol) in DMF (3 ml) is added diisopropylethylamine (0.3 ml) followed by HATU (0.155 mg, 0.55 mmol). The reaction mixture is stirred for 30 minutes at room temperature after which time a solution comprising (R)-1-(2-amino-ethyl)-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide hydrobromide [Example 49(ii)] (0.200 g, 0.37 mmol) and the resulting mixture is stirred at room temperature over night. Purification is carried out using preparative C18 column chromatography eluting with acetonitrile: water to afford the titled compound.

Workup

  1. stirringthe resulting mixture is stirred at room temperature over night
  2. customPurification
  3. washeluting with acetonitrile

Sources & evidence

ORD record
ord-67b9ccf1880b40fcae2820165331eed5
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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