Potassium sodium tartarate → HCID 59822022, compound

HRID 1645320Notes

Reaction equation

HRID 1645320 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Si:7]([O:14][C@H:15]1[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]2[N:20]=[C:19]([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[C:18]([C:32]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=3)=[O:33])=[C:17]([CH:44]3[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]3)[C:16]1=2)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[Si:7]([O:14][C@H:15]1[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]2[N:20]=[C:19]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[C:18]([C@H:32]([C:34]3[CH:35]=[CH:36][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:38][CH:39]=3)[OH:33])=[C:17]([CH:44]3[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]3)[C:16]1=2)([C:10]([CH3:11])([CH3:12])[CH3:13])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 59822023HCID 59822023, compound

Product 1

HCID 59822022HCID 59822022, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C., 10.25 ml of a 1 M solution of lithium aluminium hydride (10.25 mmol, 1.1 eq.) in THF are added dropwise to a solution of 5.72 g (9.3 mmol) of the compound from Example 4A in 116 ml of dry THF. With stirring, the mixture is warmed to room temperature over a period of 6 h. For work-up, 120 ml of a saturated sodium potassium tartrate solution are added carefully. After the evolution of gas has ceased, the mixture is extracted three times with ethyl acetate, the combined organic phases are washed with a 1:1 mixture of sodium bicarbonate solution and saturated sodium chloride solution and this aqueous phase for its part is re-extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue is purified chromatographically and at the same time separated into the diastereomers of the product (column: Chiralpak AD, 500 mm×40 mm, 20 μm; mobile phase: isohexane/isopropanol 97.5:2.5; flow rate: 50 ml/min).

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. washthe combined organic phases are washed with a 1:1 mixture of sodium bicarbonate solution and saturated sodium chloride solution
  3. extractionthis aqueous phase for its part is re-extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified chromatographically and at the same time
  8. customseparated into the diastereomers of the product (column: Chiralpak AD, 500 mm×40 mm, 20 μm; mobile phase: isohexane/isopropanol 97.5:2.5; flow rate: 50 ml/min)

Sources & evidence

ORD record
ord-3b4a8b159bc14703a94d55c0b668800d
Source dataset
uspto-grants-2012_02
Patent number
US08124775B2

Reaction notes

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