Propionic Acid → HCID 67499497, compound

HRID 1919346Notes

Reaction equation

HRID 1919346 reaction equation
Cl[CH:2]([O:6][C:7]([NH:9][CH2:10][C:11]1([CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:8])[CH2:3][CH2:4][CH3:5].[C:28]([OH:32])(=[O:31])[CH2:29][CH3:30]>C(Cl)(Cl)Cl>[C:28]([O:32][CH:2]([O:6][C:7]([NH:9][CH2:10][C:11]1([CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:8])[CH2:3][CH2:4][CH3:5])(=[O:31])[CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 1032Propionic AcidHCID 67498942HCID 67498942, compound

Product 1

HCID 67499497HCID 67499497, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of (134) (5.8 g, 14.7 mmol), propionic acid (1.64 mL, 22.0 mmol) and Ag2CO3 (6.07 g, 22.0 mmol) in chloroform (80 mL) was stirred at room temperature. The reaction was judged complete by TLC after 5 hours. The reaction mixture was then filtered through a pad of Celite, the filtrate washed with brine and dried over Na2SO4. Filtration and evaporation gave a crude product, which was purified by flash chromatography on silica gel, eluting with 15% ethyl acetate in hexane, to afford 2.5 g of title compound (135). (CDCl3, 400 MHz): δ 0.95 (t, J=7.4 Hz, 3H), 1.12 (t, J=7.4 Hz. 3H), 1.54-1.37 (in, 12H), 1.72 (m, 2H), 2.33 (m, 4H), 3.16 (dd, J=6.8, 4.4 Hz), 5.10 (s, 2H), 5.33 (t, J=6.8, 1H), 6.72 (t, J=5.8 Hz), 7.33 (m, 5H).

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of Celite
  2. washthe filtrate washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and evaporation
  5. customgave a crude product, which
  6. customwas purified by flash chromatography on silica gel
  7. washeluting with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e574e6836189420e9ecb3201c9c61ad5
Source dataset
uspto-grants-2012_05
Patent number
US08168623B2

Reaction notes

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