D-Tartaric acid → (S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate)

HRID 453682Notes

Reaction equation

HRID 453682 reaction equation
[OH:1][C@@H:2]([C@H:6]([OH:10])[C:7]([OH:9])=[O:8])[C:3]([OH:5])=[O:4].[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH:19]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:21])=[CH:14][CH:13]=1>CC(C)=O>[C:3]([C@@H:2]([O-:1])[C@@H:6]([C:7]([OH:9])=[O:8])[O-:10])([OH:5])=[O:4].[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C@@H:19]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:21])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 439655D-Tartaric acidHCID 58556923(R)-quinuclidin-3-yl 2-(4-fluorophenylamino)-2-phenylacetate

Product 1

HCID 86660298(S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate)Yield 90.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(2S,3S)-2,3-Dihydroxysuccinic acid (0.23 g, 1.52 mmol) was added to a suspension of (R)-quinuclidin-3-yl 2-(4-fluorophenylamino)-2-phenylacetate (I8) (1.08 g, 3.05 mmol) in acetone (140 ml). The resulting mixture was heated at reflux and then allowed to cool at room temperature. The precipitate was collected by filtration to obtain (S)—((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate) (689 mg, 45% yield, diastereomer 2 of 18). Evaporation of the mother solution gave (R)—((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate) (535 mg, 41% yield, diastereomer 1 of I8).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9b4eca75bee045c58f4cef736af43d9c
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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