Ethanethiol → HCID 67462095, compound

HRID 469745Notes

Reaction equation

HRID 469745 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[CH2:17][CH2:16][C:15](=[O:18])[N:14]2[C:19]2[CH:24]=[CH:23][C:22]([CH2:25][O:26]C)=[CH:21][CH:20]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(S)C.[Cl-].[Cl-].[Cl-].[Al+3]>O>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[CH2:17][CH2:16][C:15](=[O:18])[N:14]2[C:19]2[CH:20]=[CH:21][C:22]([CH2:25][OH:26])=[CH:23][CH:24]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 67953884HCID 67953884, compound

Product 1

HCID 67462095HCID 67462095, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Methoxymethyl-phenyl)-5-oxo-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide (0.130 g; 0.350 mmol) is diluted with ethanethiol (1.988 mL; 26.880 mmol) and cooled to 0° C. To this solution is added aluminum trichloride (0.793 g; 5.950 mmol). The solution is stirred for 3 hours, slowly warming to room temperature. The solution is added dropwise to a solution of water containing concentrated hydrochloric acid. The aqueous is extracted with ethyl acetate. The organics are combined and washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by preparative HPLC afforded title compound. ESI m/z 358 [M+H]+

Workup

  1. temperatureslowly warming to room temperature
  2. extractionThe aqueous is extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-0d5f98bab23148d2bd96be9da772492c
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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