Tetrahydrofuran → HCID 67814053, compound

HRID 2401363Notes

Reaction equation

HRID 2401363 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](/[CH:20]=[N:21]/[S@@:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])=[N:16][O:17][C:18]=2[CH3:19])=[O:7])=[CH:4][CH:3]=1.C1COCC1.[Cl-].[C:36]([O:40][C:41](=[O:44])[CH2:42][Zn+])([CH3:39])([CH3:38])[CH3:37]>[NH4+].[Cl-].CCOC(C)=O>[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]([C@@H:20]([NH:21][S@@:22]([C:24]([CH3:25])([CH3:26])[CH3:27])=[O:23])[CH2:42][C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:44])=[N:16][O:17][C:18]=2[CH3:19])=[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]([C@H:20]([NH:21][S@@:22]([C:24]([CH3:25])([CH3:26])[CH3:27])=[O:23])[CH2:42][C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:44])=[N:16][O:17][C:18]=2[CH3:19])=[O:7])=[CH:28][CH:29]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 88438946HCID 88438946, compoundHCID 178451183HCID 178451183, compound2×

Product 2

HCID 67814053HCID 67814053, compoundHCID 67815301HCID 67815301, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a round bottomed flask was added (R,E)-N-((4-(2-(4-chlorobenzoyl)phenyl)-5-methylisoxazol-3-yl)methylene)-2-methylpropane-2-sulfinamide (0.480 g, 1.12 mmol) and THF (6 mL). This solution was cooled to 0° C. before addition of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (4.48 mL, 2.24 mmol). The solution was stirred at 0° C. before for 3.5 h before addition of more of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (1.12 mL, 0.560 mmol). The reaction was stirred for an additional 2.5 h before being diluted with aqueous NH4Cl and EtOAc. The layers were separated and the aqueous was 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)-5-methylisoxazol-3-yl)-3-((R)-1,1-dimethylethylsulfinamido)propanoate (0.118 g, 0.216 mmol) and (3R)-tert-butyl 3-(4-(2-(4-chlorobenzoyl)phenyl)-5-methylisoxazol-3-yl)-3-((R)-1,1-dimethylethylsulfinamido)propanoate (0.094 g, 0.172 mmol). LC/MS m/z 545 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-20fab3008a564b698879f1f7dda370b7
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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