Sodium Thiosulfate → HCID 86667491, compound

HRID 2368045Notes

Reaction equation

HRID 2368045 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:26]2[CH2:28][CH2:27]2)[N:9]2[CH2:14][CH2:13][C:12]([CH2:21][C:22]([CH3:24])=[CH2:23])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:11][C:10]2=[O:25])=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:34].[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:26]2[CH2:28][CH2:27]2)[N:9]2[CH2:14][CH2:13][C:12]([CH2:21][C:22]3([CH3:24])[CH2:23][O:34]3)([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:11][C:10]2=[O:25])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 68759724HCID 68759724, compound

Product 1

HCID 86667491HCID 86667491, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
5 °C

Procedure

3-[(4-Bromo-phenyl)-cyclopropyl-methyl]-6-(2-methyl-allyl)-6-phenyl-[1,3]oxazinan-2-one (diastereomer 2 from Step 3; 1.60 g) dissolved in dichloromethane (15 mL) was added to a solution of 3-chloroperoxybenzoic acid (77%, 0.94 g) in dichloromethane (15 mL) cooled to 5° C. The solution was stirred at room temperature for 3 h, before another portion of 3-chloroperoxybenzoic acid (77%, 0.13 g) was added. After stirring the solution at room temperature for another 1.5 h, aqueous 10% Na2S2O3 solution (10 mL) and aqueous saturated NaHCO3 solution (10 mL) were added and the resulting mixture was stirred for further 30 min. Dichloromethane (20 mL) was added and the organic phase was separated and washed with a 1:1 mixture of aqueous 10% Na2S2O3 solution and aqueous saturated NaHCO3 solution. Then the organic phase was washed with water, dried (MgSO4), and concentrated to furnish the title compound. Yield: 1.86 g (ca. 85-90% pure, quantitative); LC-MS (Method 1): tR=4.00 min; Mass spectrum (ESI+): m/z=456/458 (Br) [M+H]+.

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred for further 30 min
  3. customthe organic phase was separated
  4. washwashed with a 1:1 mixture of aqueous 10% Na2S2O3 solution and aqueous saturated NaHCO3 solution
  5. washThen the organic phase was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6e717cb860a24f818a65e6140c773ea5
Source dataset
uspto-grants-2014_04
Patent number
US08703765B2

Reaction notes

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