Methyl acetoacetate → HCID 54721634, compound

HRID 481871Notes

Reaction equation

HRID 481871 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:11]([Li])CCC.[CH2:16]([CH2:23][NH:24][C:25](=[O:37])[CH2:26][CH2:27][CH2:28][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19]C=1>CCCCCC.O1CCCC1>[CH2:23]([N:24]([CH3:11])[C:25](=[O:37])[CH2:26][CH2:27][CH2:28][C:29]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:5][C:3]([OH:4])=[CH:2][C:1](=[O:6])[O:36]1)[C:16]1[CH:17]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 20969092HCID 20969092, compoundHCID 178418339Butyllithium

Product 1

HCID 54721634HCID 54721634, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared as described in General Method 1 using 5.6 mmol of methyl acetoacetate, 6.1 mmol of NaH 60% dispersion in oil, 5.9 mmol of 1.6M n-butyl lithium in hexane, 5.6 mmol of 5-oxo-5-phenylpentanoic acid benzylmethyl amide and 25 mL of tetrahydrofuran. The product was flash chromatographed using CH2 Cl2 /MeOH (98/2) to give a solid (m.p. 47°-51° C.). 1H NMR (DMSO-d6) δ1.1-1.3 (m, 1H), 1.4-1.6 (m, 1H), 1.8-2.0 (m, 2H), 2.2-2.4 (m, 2H), 2.75/2.81 (s/s 3H), 2.85-3.1 (m, 2H), 4.4/4.5 (s/s, 2H), 4.85/4.9 (s/s 1H), 7.1-7.4 (m, 10H), 11.36/11.38 (s/s, 1H).

Workup

  1. customchromatographed

Sources & evidence

ORD record
ord-f4fa41314878446b89bd31b5bee26e1a
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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