Acetic Acid → 5-tert-butoxy-5-oxo-3-[(phenylthio)methyl]pentanoic Acid

HRID 585565Notes

Reaction equation

HRID 585565 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][CH:8]1[CH2:12][C:11](=[O:13])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C>CN(C)C=O.C1COCC1.O>[C:1]([O:5][C:6](=[O:14])[CH2:7][CH:8]([CH2:9][S:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][C:11]([OH:10])=[O:13])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 7969ThiophenolHCID 13641874Tert-butyl (5-oxotetrahydrofuran-3-yl)acetate

Product 1

HCID 219278795-tert-butoxy-5-oxo-3-[(phenylthio)methyl]pentanoic AcidYield 35%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

The product from step 1 (200 mg, 1.0 mmoles) and thio phenol (110 mg, 1 mmoles) were combined in dimethyl formamide (1.5 mL) at room temperature. Lithium(bis trimethyl silyl)amide (1.25 mL of a 1M solution in THF) was added and the reaction heated at 80° C. for 18 h. Reaction was diluted with water, made acidic with acetic acid and extracted with dichloromethane 2×40 mL. The combined extracts were washed with water 2×50 mL, brine 1×50 mL, dried and the solvent removed under pressure. The crude was chromatographed to give the product 108 mg (35%). MS (ESI+) for C16H22O4S m/z 333 (M+Na)+.

Workup

  1. customReaction
  2. extractionextracted with dichloromethane 2×40 mL
  3. washThe combined extracts were washed with water 2×50 mL, brine 1×50 mL
  4. customdried
  5. customthe solvent removed under pressure
  6. customThe crude was chromatographed

Sources & evidence

ORD record
ord-fd51bf03358a4295b5a636fa13f435d4
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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