Methyl acetoacetate → HCID 70254579, compound

HRID 356492Notes

Reaction equation

HRID 356492 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35](C(=O)CCC3C=CC=CC=3)=[CH:34][CH:33]=2)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:16]([O:20][C:21]([N:23]1[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][O:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=2[C:8]2([CH2:14][CH2:13][C:12]3[CH:11]=[CH:5][CH:3]=[CH:2][CH:1]=3)[CH2:5][C:3]([OH:4])=[CH:2][C:1](=[O:6])[O:7]2)[CH2:27][CH2:28]1)=[O:22])([CH3:17])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 53717435HCID 53717435, compoundHCID 178418339Butyllithium

Product 1

HCID 70254579HCID 70254579, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared as described in General Method 6 using 37.2 g (320 mmol) of methyl acetoacetate, 13.2 g (330 mmol) of sodium hydride (60% dispersion in oil), 200 mL of 1.6M n-butyllithium (320 mmol), 70.2 g (160 mmol) of 4-{2-[4-(3-phenyl-propionyl)-phenoxy]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester prepared in Example W, and 400 mL of THF. After addition of the ketone, the reaction mixture was stirred at 1 hour at 0° C. and then quenched with a 50:50 mixture of acetic acid:H2O. Standard work-up gave the crude aldol product which was carried on without purification.

Workup

  1. customquenched with a 50:50 mixture of acetic acid
  2. customStandard work-up gave the crude aldol product which
  3. customwas carried on without purification

Sources & evidence

ORD record
ord-403c376d1bb94f66a2bb60f3cb457272
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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