Ethanol → HCID 57344511, compound

HRID 2401360Notes

Reaction equation

HRID 2401360 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:15]([CH3:35])=[N:16][O:17][C:18]=2[C@@H:19]([NH:28][S@@](C(C)(C)C)=O)[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=O)=[CH:4][CH:3]=1.CCO.C(Cl)(=O)C>C([O-])(O)=O.[Na+].CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:14]3[C:15]([CH3:35])=[N:16][O:17][C:18]=3[C@H:19]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[N:28]=2)=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 67814081HCID 67814081, compound

Product 1

HCID 57344511HCID 57344511, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

To a resealable vial was added (3S)-tert-butyl 3-(4-(2-(4-chlorobenzo yl)phenyl)-3-methylisoxazol-5-yl)-3-((R)-1,1-dimethylethylsulfinamido)propanoate (0.043 g, 0.079 mmol), EtOH (3 mL), and acetyl chloride (0.017 mL, 0.237 mmol). The vial was sealed and heated to 60° C. for 1.75 h before being cooled to room temperature and diluting with saturated NaHCO3 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 tert-butyl 2-((4S)-6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepin-4-yl)acetate (0.026 g, 0.061 mmol). 1H NMR (400 MHz, Acetone-d6) δ 7.87-7.83 (m, 1H), 7.76-7.70 (m, 1H), 7.51-7.41 (m, 2H), 7.40 (s, 4H), 4.40 (br. s, 1H), 3.32 (d, J=7.19 Hz, 2H), 2.54 (s, 3H), 1.48 (s, 9H); LC/MS m/z 423 [M+H]+.

Workup

  1. customThe vial was sealed
  2. temperaturebefore being cooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous was 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-bc30708d9880475a93492fb483c8d51f
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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