2,3-Dihydroxybutanedioic Acid → HCID 10053080, compound

HRID 218336Notes

Reaction equation

HRID 218336 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[CH2:8][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=1[CH:20]=[CH:21][C:22](=[O:29])[NH:23]3)[OH:17])[CH2:6]2)[CH3:2].[C:30]([OH:39])(=[O:38])[CH:31]([CH:33]([C:35]([OH:37])=[O:36])[OH:34])[OH:32]>C(O)(C)C>[C:35]([CH:33]([CH:31]([C:30]([OH:39])=[O:38])[OH:32])[OH:34])([OH:37])=[O:36].[CH2:12]([C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[CH2:1][CH3:2])[CH2:6][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]3[C:19]=1[CH:20]=[CH:21][C:22](=[O:29])[NH:23]3)[OH:17])[CH2:8]2)[CH3:13]

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 6918554Indacaterol

Product 1

HCID 10053080HCID 10053080, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 2.0 g (R)-5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one base (5.10 mmoles) in 14 ml isopropanol is heated at 50° C. Then a solution of 0.77 g L (+) tartaric acid (5.10 mmoles) in 7.7 ml isopropanol is dropwise added over ca. 2 minutes. The suspension is stirred at 50° C. for 15 hours. The white suspension is cooled to ca. 25° C. and filtered. The salt is washed with 10 ml isopropanol and dried for 18 hours/50° C./ca. 10 mbar and for 2 hours at 60° C./ca. 1 mbar. Yield: 2.33 g white powder (84.27%)

Workup

  1. temperatureThe white suspension is cooled to ca. 25° C.
  2. filtrationfiltered
  3. washThe salt is washed with 10 ml isopropanol
  4. customdried for 18 hours/50° C./ca. 10 mbar
  5. waitfor 2 hours at 60° C./ca. 1 mbar

Sources & evidence

ORD record
ord-25bc46d6952645cca36597fcbed944c2
Source dataset
uspto-grants-2012_06
Patent number
US08198450B2

Reaction notes

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