Triethylamine → HCID 86592945, compound

HRID 1245398Notes

Reaction equation

HRID 1245398 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH:4]=[CH:5][CH:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:29])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:7]1.[C:31]([OH:34])(=[S:33])[CH3:32].C(N(CC)CC)C>>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH:5]([S:33][C:31](=[O:34])[CH3:32])[CH:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:29])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:7]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 69640073HCID 69640073, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86592945HCID 86592945, compoundYield 63%

Procedure

A suspension of the product from step 11a (1.0 g, 2.5 mmol), thioacetic acid (3.0 mL), and triethylamine (0.25 mL, 1.8 mmol) was stirred for 6 h at room temperature while slowly becoming a clear solution. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium bicarbonate (2×), brine, dried over magnesium sulfate, and concentrated to give the crude product. This was purified by FCC on silica gel eluting ethyl acetate:hexanes (gradient) to give 3-acetylsulfanyl-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester (0.74 g, 63%) as an oil. MS found: (M+H)+=479.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with aqueous sodium bicarbonate (2×), brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThis was purified by FCC on silica gel
  7. washeluting ethyl acetate

Sources & evidence

ORD record
ord-d1e9e5bb369e4743a6a550c16ce11e28
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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