Ethyl Acetate → HCID 57101162, compound

HRID 544554Notes

Reaction equation

HRID 544554 reaction equation
[CH:1]1([C:5]([N:7]2[CH2:31][CH2:30][C@:14]34[C:15]5[C:16]6[O:29][CH:13]3[C:12]3([O:35][CH2:34][CH2:33][O:32]3)[CH2:11][CH2:10][C@@:9]4([F:36])[C@H:8]2[CH2:21][C:20]=5[CH:19]=[CH:18][C:17]=6[O:22]C(C2CCC2)=O)=O)[CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.C(=O)(O)[O-].[K+]>O1CCCC1.O>[CH:1]1([CH2:5][N:7]2[CH2:31][CH2:30][C@:14]34[C:15]5[C:16]6[O:29][CH:13]3[C:12]3([O:32][CH2:33][CH2:34][O:35]3)[CH2:11][CH2:10][C@@:9]4([F:36])[C@H:8]2[CH2:21][C:20]=5[CH:19]=[CH:18][C:17]=6[OH:22])[CH2:2][CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516893Potassium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 70504925HCID 70504925, compound

Product 1

HCID 57101162HCID 57101162, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above obtained amide ester (step b) was heated with lithium aluminum hydride (1 g) in tetrahydrofuran (50 ml) at reflux for 31/2 hours. After cooling the reaction mixture, the excess reducing agent was decomposed by adding ethyl acetate, then water, and then dilute potassium bicarbonate solution until the pH was ca. 8.5. The inorganic salts were filtered off, and the filter cake washed with hot tetrahydrofuran. The filtrate was evaporated to dryness and the residue washed thoroughly with water and air dried. Recrystallization from methanol yielded 700 mg of the title compound whch melted at 173°-174°.

Workup

  1. temperatureat reflux for 31/2 hours
  2. temperatureAfter cooling the reaction mixture
  3. filtrationThe inorganic salts were filtered off
  4. washthe filter cake washed with hot tetrahydrofuran
  5. customThe filtrate was evaporated to dryness
  6. washthe residue washed thoroughly with water and air
  7. customdried
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-9c349071079c445b8ad44f8e737b8bba
Source dataset
uspto-grants-1984_05
Patent number
US04451470

Reaction notes

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