Aluminum(III) Chloride → HCID 70865321, compound

HRID 336199Notes

Reaction equation

HRID 336199 reaction equation
C[O:2][CH2:3][C:4]([C:7]1[O:11][N:10]=[C:9]([NH:12][C:13]([C@@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][N:16]2[C:21]([N:23]2[CH2:28][CH2:27][S:26](=[O:30])(=[O:29])[CH2:25][CH2:24]2)=[O:22])=[O:14])[CH:8]=1)([CH3:6])[CH3:5].[Cl-].[Al+3].[Cl-].[Cl-]>C(S)C>[OH:2][CH2:3][C:4]([C:7]1[O:11][N:10]=[C:9]([NH:12][C:13]([C@@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][N:16]2[C:21]([N:23]2[CH2:28][CH2:27][S:26](=[O:29])(=[O:30])[CH2:25][CH2:24]2)=[O:22])=[O:14])[CH:8]=1)([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 46873308HCID 46873308, compound

Product 1

HCID 70865321HCID 70865321, compound

Reagents, catalysts & solvents 1

HCID 6343EthanethiolSolvent

Conditions

Temperature
0 °C

Procedure

(S)-1-(1,1-Dioxo-1λ6-thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid [5-(2-methoxy-1,1-dimethyl-ethyl)-isoxazol-3-yl]-amide (110 mg; 0.249 mmol) is dissolved in ethanethiol (2 mL) and cooled to 0° C. Aluminum chloride (498 mg; 3.735 mmol) is added to the solution and the reaction mixture is stirred at room temperature for 2 hours. The mixture is quenched with water (10 mL) and 3 drops of concentrated HCl aqueous solution and extracted with ethyl acetate 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated. Purification by preparative HPLC affords title compound, m/z 429 [M+H+].

Workup

  1. customThe mixture is quenched with water (10 mL) and 3 drops of concentrated HCl aqueous solution
  2. extractionextracted with ethyl acetate 3 times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-106acbfa473e45b491abb650c16a629d
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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