Ethyl Acetate → HCID 19900671, compound

HRID 1029532Notes

Reaction equation

HRID 1029532 reaction equation
ClC1C=CC=C([C:8](OO)=[O:9])C=1.[CH3:12][C:13]([C:16]1[CH:17]=[C:18]([S:27][CH2:28][CH2:29][C:30]([NH:32][NH2:33])=[O:31])[CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[OH:22])([CH3:15])[CH3:14].C(OCC)(=[O:36])C>ClCCl>[CH3:15][C:13]([C:16]1[CH:17]=[C:18]([S:27]([CH2:28][CH2:29][C:30]2[O:31][C:8](=[O:9])[NH:33][N:32]=2)=[O:36])[CH:19]=[C:20]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:21]=1[OH:22])([CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 19609556HCID 19609556, compound

Product 1

HCID 19900671HCID 19900671, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

m-Chloroperbenzoic acid (1.30 g, 6.0 mmol) is added in eight portions at 5-minute intervals to a 0° C. solution of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanoic acid hydrazide (2.25 g, 6.4 mmol) in dichloromethane (64 mL). The reaction mixture is stirred at 0° C. for 2.25 hours, then diluted with ethyl acetate and washed three times with a saturated solution of sodium bicarbonate, then with water and brine. Drying the organic phase over magnesium sulfate and evaporation gives a crude product which is chromatographed on a column of silica with ethyl acetate/hexane (3/1) to afford 1.92 g of a glassy solid.

Workup

  1. washwashed three times with a saturated solution of sodium bicarbonate
  2. customDrying the organic phase
  3. customover magnesium sulfate and evaporation
  4. customgives a crude product which
  5. customis chromatographed on a column of silica with ethyl acetate/hexane (3/1)

Sources & evidence

ORD record
ord-6b143cc1145a4976b44d39015147b0b2
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

Loading…