HCID 88439250, compound → HCID 67814081, compound

HRID 2401359Notes

Reaction equation

HRID 2401359 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:15]([CH3:27])=[N:16][O:17][C:18]=2/[CH:19]=[N:20]/[S@@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])=[O:7])=[CH:4][CH:3]=1.[Cl-].[C:31]([O:35][C:36](=[O:39])[CH2:37][Zn+])([CH3:34])([CH3:33])[CH3:32]>C1COCC1.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:15]([CH3:27])=[N:16][O:17][C:18]=2[C@@H:19]([NH:20][S@@:21]([C:23]([CH3:25])([CH3:24])[CH3:26])=[O:22])[CH2:37][C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:39])=[O:7])=[CH:28][CH:29]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:15]([CH3:27])=[N:16][O:17][C:18]=2[C@H:19]([NH:20][S@@:21]([C:23]([CH3:25])([CH3:24])[CH3:26])=[O:22])[CH2:37][C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:39])=[O:7])=[CH:28][CH:29]=1

Participants

6

Reactant 2

HCID 88439250HCID 88439250, compoundHCID 178451183HCID 178451183, compound

Product 2

HCID 67814081HCID 67814081, compoundHCID 67815302HCID 67815302, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottomed flask was added (R,E)-N-((4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)methylene)-2-methylpropane-2-sulfinamide (0.083 g, 0.194 mmol) in THF (0.5 mL). This solution was cooled to 0° C. before addition of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (0.464 mL, 0.232 mmol) and stirring at 0° C. for 1 h before addition of another more zinc reagent (0.388 mL, 0.194 mmol). After stirring 3 h at 0° C. the solution was quenched with aqueous ammonium chloride solution and EtOAc added. The layers were separated and the aqueous extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (3S)-tert-butyl 3-(4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)-3-((R)-1,1-dimethylethylsulfinamido)propanoate (Rf (1:1 EtOAc:hex)=˜0.3, Mass: 0.043 g, LC/MS m/z 545 [M+H]+) and (3R)-tert-butyl 3-(4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)-3-((R)-1,1-dimethylethylsulfinamido)propanoate (Rf (1:1 EtOAc:hex)=˜0.15, Mass: 0.045 g, LC/MS m/z 545 [M+H]+).

Workup

  1. customwas quenched with aqueous ammonium chloride solution and EtOAc
  2. additionadded
  3. customThe layers were separated
  4. extractionthe aqueous extracted with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-f9708220081f4fc2910f5b70d0cffedc
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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