Maleic Acid → HCID 68429484, compound

HRID 1993481Notes

Reaction equation

HRID 1993481 reaction equation
[OH:1][C@@H:2]1[C@@H:15]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]2[CH:13]=[C:12]3[C:7]([NH:8][C:9](=O)[CH2:10][O:11]3)=[CH:6][C:5]=2[O:4][C:3]1([CH3:27])[CH3:26].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])O.[Na+].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43]>O1CCCC1.C(OCC)(=O)C.CCCCCC>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[CH3:26][C:3]1([CH3:27])[C@H:2]([OH:1])[C@@H:15]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]2[CH:13]=[C:12]3[C:7]([NH:8][CH2:9][CH2:10][O:11]3)=[CH:6][C:5]=2[O:4]1

Participants

8

Reactant 4

HCID 444266Maleic AcidHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 59134293HCID 59134293, compound

Product 1

HCID 68429484HCID 68429484, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (7R*,8S*)-7-hydroxy-6,6-dimethyl-8-[(2-phenylethyl)amino]-4,6,7,8-tetrahydro-1,5-dioxa-4-aza-anthracene-3-one (42 mg, 0.11 mmol) in tetrahydrofuran (1.2 mL), lithium aluminum hydride (1M solution in tetrahydrofuran, 570 μL, 0.57 mmol) was added at room temperature, and the resulting mixture was stirred at 90° C. for 1.5 hour. Upon the completion of the reaction, saturated aqueous sodium hydrogencarbonate solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Maleic acid (13 mg, 0.11 mmol) and hexane (1 mL) were added to the solution of the resulting mixture in ethyl acetate (600 μL) at room temperature, and the resulting mixture was stirred at room temperature for 15 minutes. The resulting crystal was filtered off and the aimed product was obtained (yield: 60%).

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. stirringthe resulting mixture was stirred at room temperature for 15 minutes
  7. filtrationThe resulting crystal was filtered off

Sources & evidence

ORD record
ord-befbec11689044bd8fe773742b05423a
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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