2,2,4-Trimethylpentane → HCID 9967975, compound

HRID 343087Notes

Reaction equation

HRID 343087 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:13][O:14][C:15]=2[CH2:16][C:17](O)=[O:18])=[CH:7][CH:6]=1)(=[O:4])=[O:3].CSC.B.C(CC(C)(C)C)(C)C>C1COCC1.ClCCl>[OH:18][CH2:17][CH2:16][C:15]1[O:14][N:13]=[C:12]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:11]=1[C:8]1[CH:7]=[CH:6][C:5]([S:2]([NH2:1])(=[O:4])=[O:3])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 109072,2,4-TrimethylpentaneHCID 12423031(Dimethyl sulfide)trihydroboronHCID 19608691HCID 19608691, compound

Product 1

HCID 9967975HCID 9967975, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [4-[4-(aminosulfonyl)phenyl]-3-phenylisoxazol-5-yl]acetic acid (Step 1) (0.85 g, 2.37 mmol) in THF (25 mL) was added borane dimethylsulfide (0.47 mL of 10.0M solution, 4.74 mmol). After stirring at room temperature for 2 days, the reaction was quenched with aqueous KHSO4 (0.25M) and extracted with ethyl acetate. The combined ethyl acetate phases were washed with saturated NaHCO3 solution, brine, dried over MgSO4, filtered and concentrated in vacuo yielding a pale yellow solid. The crude product was dissolved in hot dichloromethane and isooctane was added to induce crystallization. Vacuum filtration of the resulting suspension yielded 4-[5-(2-hydroxyethyl)-3-phenylisoxazol-4-yl]benzenesulfonamide (0.276 g, 34%) as a pale yellow solid: mp 186°-190° C. 1H NMR (DMSO d6 /300 MHz) 7.81 (d, 2H, J=8.0 Hz), 7.48-7.28 (m, 9H), 4.95 (t, 1H, J=5.0 Hz), 3.70 (q, 2H, J=5.6 Hz), 2.92 (t, 2H, J=6.2 Hz). FABLRMS m/z 345 (M+H). FABHRMS m/z 345.0923 (M+H, C17H17N2O4S requires 345.0909). Anal. Calc'd for C17H17N2O4S.1.66 wt % H2O: C. 58.30; H, 4.79; N, 8.00. Found: C, 58.37; H, 4.89; N, 7.60.

Workup

  1. customthe reaction was quenched with aqueous KHSO4 (0.25M)
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate phases were washed with saturated NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customyielding a pale yellow solid
  8. customcrystallization
  9. filtrationVacuum filtration of the resulting suspension

Sources & evidence

ORD record
ord-9dbcff372fdb4f709d9a09f920ff0f87
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

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