Tetrahydrofuran → HCID 69735894, compound

HRID 481099Notes

Reaction equation

HRID 481099 reaction equation
C(O[C:4](=O)[CH:5]([C:16]1[C:21]([NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[CH:20][CH:19]=[C:18]([O:33][CH3:34])[N:17]=1)S(C1C=CC(C)=CC=1)(=O)=O)C.[CH3:36][C:37](C)([O-:39])C.[K+].C1C[O:45][CH2:44]C1>>[CH2:37]([O:39][C:44](=[O:45])[CH:4]=[CH:5][C:16]1[C:21]([NH:22][C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])=[CH:20][CH:19]=[C:18]([O:33][CH3:34])[N:17]=1)[CH3:36]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxideHCID 69736562HCID 69736562, compound

Product 1

HCID 69735894HCID 69735894, compound

Procedure

To a cooled (5° C.) solution of 15.7 g (0.031 mol) of (3-benzyloxycarbonylamino-6-methoxy-pyridin-2-yl)-(toluene-4-sulfonyl)-acetic acid ethyl ester dissolved in 160 mL of THF is added, dropwise, 31 mL of a 1N solution of potassium-t-butoxide dissolved in THF. The reaction mixture is warmed to room temperature and stirred for 2 hours. The reaction is quenched with 5 mL of water and evaporated. The residue is dissolved in 200 mL of ethyl acetate and 200 mL of water. The ethyl acetate layers are dried (Na2SO4) and evaporated. The residue is chromatographed on 375 grams of silica gel using 7/3 hexanes/ethyl acetate as the eluant. Appropriate fractions are combined and evaporated to yield 5.57 grams of 3-[3-benzyloxycarbonylamino-6-methoxy-pyridin-2-yl]-acrylic acid ethyl ester. 1H NMR (CDCl3) δ7.8 (m, 2H), 7.4 (m, 2H), 7.0 (m, 1H), 6.8 (m, 1H), 6.7 (m, 1H), 5.2 (s, 2H), 4.2 (q, 2H) 3.9 (s, 3H), 1.3 (t, 3H). Mass spectrum: m/e=357 (p+1).

Workup

  1. additionis added
  2. customThe reaction is quenched with 5 mL of water
  3. customevaporated
  4. dissolutionThe residue is dissolved in 200 mL of ethyl acetate
  5. dry with materialThe ethyl acetate layers are dried (Na2SO4)
  6. customevaporated
  7. customThe residue is chromatographed on 375 grams of silica gel using 7/3 hexanes/ethyl acetate as the eluant
  8. customevaporated

Sources & evidence

ORD record
ord-b412a5019ec64735a41fee4e137c20ad
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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