Ethyl Acetate → HCID 118022352, compound

HRID 575673Notes

Reaction equation

HRID 575673 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23](F)[CH:24]=3)[C:19](=[O:27])[N:18]([CH3:28])[CH:17]=2)[CH2:3][CH2:2]1.C[O-].[Na+].C[C:33](=O)[O:34]CC>CN(C)C(=O)C.CO.CCCCCC>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:34][CH3:33])[CH:24]=3)[C:19](=[O:27])[N:18]([CH3:28])[CH:17]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 118021461HCID 118021461, compound

Product 1

HCID 118022352HCID 118022352, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8058HexaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
85 °C

Procedure

The title compound of Example 90, step 2 (30 mg, 0.075 mmol) in N,N-dimethylacetamide was treated with excess 25% sodium methoxide in methanol and heated at 85° C. until complete. Silica gel chromatography (40-80% EA in hexane over 8 min, then isocratic) gave the title compound 23 mg, 0.056 mmol, 74%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.06-0.20 (m, 2H) 0.27-0.43 (m, 2H) 0.83-1.05 (m, 1H) 3.22 (s, 3H) 3.53 (s, 3H) 3.73 (s, 3H) 3.83-4.16 (m, 2H) 6.47 (s, 1H) 7.04-7.20 (m, 1H) 7.36 (d, J=8.59 Hz, 1H) 7.50 (s, 1H) 7.81 (s, 1H) 7.96 (d, J=6.82 Hz, 1H) 8.23 (d, J=8.59 Hz, 1H). LCMS: 414 (M+H)+

Sources & evidence

ORD record
ord-4be6389ec1ff42dab0086c7beced5768
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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