Diisopropylcarbodiimide → (2-(1Azabicyclo[2.2.2]oct-3yl)acetoxy}-2,3,5,6-tetrafluorobenzoic acid

HRID 55773Notes

Reaction equation

HRID 55773 reaction equation
[OH:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:13])[C:3]=1[F:14].Cl.[N:16]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[CH:18]([CH2:24][C:25](O)=[O:26])[CH2:17]2.C(N=C=NC(C)C)(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[N:16]12[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23]1)[CH:18]([CH2:24][C:25]([O:1][C:2]1[C:3]([F:14])=[C:4]([F:13])[C:5]([C:6]([OH:8])=[O:7])=[C:9]([F:12])[C:10]=1[F:11])=[O:26])[CH2:17]2

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 98835Tetrafluoro-4-hydroxybenzoic acidHCID 230241472-(Quinuclidin-3-yl)acetic acid hydrochloride

Product 1

HCID 17979834(2-(1Azabicyclo[2.2.2]oct-3yl)acetoxy}-2,3,5,6-tetrafluorobenzoic acidYield 235.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

2 g of the polymeric support resin from Example 8A (loading about 1.36 mmol/g, 2.72 mmol) are suspended in 20 ml of DMF and shaken with 1.23 g (5.98 mmol) of 1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride and 130 mg (1.09 mmol) of DMAP for 10 min. Then 1.06 ml (6.80 mmol) of N,N′-diisopropylcarbodiimide are added, and the mixture is shaken overnight. The resin is filtered off with suction, washed twice each with 20 ml each of DMF, THF and DCM and dried under high vacuum. 2.318 g of the polymer-bound title compound are obtained.

Workup

  1. filtrationThe resin is filtered off with suction
  2. washwashed twice each with 20 ml each of DMF, THF and DCM
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-6992c5cb27204b3e83ffb979c478ad2b
Source dataset
uspto-grants-2016_09
Patent number
US09433614B2

Reaction notes

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