Hydrogen Peroxide → HCID 86586091, compound

HRID 2417251Notes

Reaction equation

HRID 2417251 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[OH:23]O>CO>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S@@:12]([C@@H:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:14]([OH:16])=[O:15])=[O:23])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 11186284HCID 11186284, compound

Product 1

HCID 86586091HCID 86586091, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(4-But-2-ynyloxy-phenylsulfanyl)-octanoic acid hydroxamide (prepared in Example 6) (1.78 g, 5 mmol) was dissolved in methanol (50 ml) and H2O2 (30%, 10 ml) was added. The reaction mixture was stirred at room temperature for 96 hours and quenched with ice cold solution of NaHSO3 solution. The reaction mixture was concentrated under reduced pressure and the residue was extracted with chloroform. Examination of the reaction mixture showed the formation of two diastereo isomers and they were separated by silica-gel column chromatography by eluting it with 50% ethyl acetate; hexane. 411 g of (S)-2-[(R)-4-but-2-ynyloxy-phenylsulfinyl)-octanoic acid hydroxamide was isolated as a white solid, mp 132.3° C.; Yield 24%; MS: 352.0 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ 0.834 (m, 3H), 1.19 (m, 9H), 1.76 (m, 1H), 1.84(t, 3H), 3.11-3.17 (dd, 2H), 3.33 (t, 3H), 4.81 (d, 2H) 7.15 (d, J=2.8, 2H), 7.36 (d, J=2.3, 2H), 9.00 (s, 1H), 10.56 (s, 1H).

Workup

  1. customquenched with ice cold solution of NaHSO3 solution
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionthe residue was extracted with chloroform
  4. customwere separated by silica-gel column chromatography
  5. washby eluting it with 50% ethyl acetate

Sources & evidence

ORD record
ord-c6ae729f45ee4699878074990e29bcd8
Source dataset
uspto-grants-2004_11
Patent number
US06825354B2

Reaction notes

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