HCID 10774139, compound → HCID 21927928, compound

HRID 585544Notes

Reaction equation

HRID 585544 reaction equation
[NH2:1][C:2](=[S:12])[CH2:3][C:4]([CH3:11])([CH3:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].O.O.O.O.O.[OH-].C(=O)(O)[O-].[Mg+2].[C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](=O)[CH2:33]Cl)(=[O:26])[CH3:25]>O1CCOCC1.C(OCC)(=O)C>[C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[N:1]=[C:2]([CH2:3][C:4]([CH3:10])([CH3:11])[CH2:5][C:6]([O:8][CH3:9])=[O:7])[S:12][CH:33]=1)(=[O:26])[CH3:25]

Participants

6

Reactant 3

HCID 10774139HCID 10774139, compound2×HCID 21927861HCID 21927861, compoundHCID 5324963056378-72-4

Product 1

HCID 21927928HCID 21927928, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 5-amino-3,3-dimethyl-5-thioxopentanoate (500 mg; 2.64 mmoles) was dissolved in 1,4-dioxane (10 mL) under nitrogen and magnesium carbonate hydroxide pentahydrate (640 mg; 1.32 mmoles) was added. 6-Chloro-5-oxohexyl acetate (685 mg; 3.56 mmoles; Rieke, R. D.; Brown, J. D.; Wu, X. Synth. Commun. 1995, 25(23), 3923.) was added and the mixture was magnetically stirred for 10 hours with heating to 60° C. The mixture was allowed to cool, diluted with ethyl acetate and filtered. The solvent was removed under vacuum and the residue was purified by chromatography on silica gel, eluting with hexane/ethyl acetate (3:1). Following removal of solvent the product, methyl 4-{4-[4-(acetyloxy)butyl]-1,3-thiazol-2-yl}-3,3-dimethylbutanoate, was obtained as pale yellow oil. (820 mg). The material was impure, containing some 6-Chloro-5-oxohexyl acetate. 1H NMR (400 MHz) CDCl3 δ 6.76 (1H, s), 4.04-4.11 (2H, m), 3.68 (3H, m), 3.05 (2H, s), 2.78 (2H, t, J=7.5 Hz), 2.33 (2H, s), 2.04 (3H, s), 1.61-1.82 (4H, m), 1.10 (6H, s).

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromatography on silica gel
  5. washeluting with hexane/ethyl acetate (3:1)
  6. customremoval of solvent the product, methyl 4-{4-[4-(acetyloxy)butyl]-1,3-thiazol-2-yl}-3,3-dimethylbutanoate
  7. customwas obtained as pale yellow oil

Sources & evidence

ORD record
ord-9b9802d4568b4b198898f0775587486a
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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