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Potassium bisulfate → HCID 88414407, compound

HRID 1963087
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Reaction equation

HRID 1963087 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:20]3[N:21]=[CH:22][C:23]([C:25](=[O:30])N(OC)C)=[CH:24][C:19]3=[C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:17]=2[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=2[CH3:45])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].S([O-])(O)(=O)=O.[K+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:16]2[N:20]3[N:21]=[CH:22][C:23]([CH:25]=[O:30])=[CH:24][C:19]3=[C:18]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:17]=2[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=2[CH3:45])=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 88414359HCID 88414359, compound

Product 1

HCID 88414407HCID 88414407, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a solution of the compound of step 1 (0.990 g, 1.61 mmol) in 11 ml of anhydrous THF, cooled to 0° C. under an atmosphere of nitrogen, was added a 1 M solution of lithium tri-tert-butoxy-aluminium hydride in THF. The mixture was stirred at 0-5° C. for 3.5 h. Then a 0.5 M aqueous solution of potassium hydrogensulfate (20 ml) was added, the mixture was vigorously stirred for 1 min and then extracted twice with EA (30 ml). The combined organic phases were washed with a saturated solution of sodium hydrogencarbonate (20 ml) and brine (40 ml), dried over magnesium sulfate and evaporated to dryness. The residue was purified by chromatography on silica gel (cyclohexane/EA, 70:30, then 65:35) to give 0.363 g of the title compound as a yellow solid melting at 208-209° C.

Workup

  1. stirringthe mixture was vigorously stirred for 1 min
  2. extractionextracted twice with EA (30 ml)
  3. washThe combined organic phases were washed with a saturated solution of sodium hydrogencarbonate (20 ml) and brine (40 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 70:30

Sources & evidence

ORD record
ord-e8daa694b31449dfa071731370f81afd
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415336B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes