Tetrahydrofuran → HCID 21069288, compound

HRID 1244104Notes

Reaction equation

HRID 1244104 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([O:22]CC)=O)=[CH:14][CH:13]=2)=[CH:10][S:9][C:8]=1[NH2:25])=[O:6])[CH3:3].[CH2:26]([Mg]Cl)[CH:27]=[CH2:28].[CH2:31]1[CH2:35]OC[CH2:32]1>>[CH2:2]([O:4][C:5]([C:7]1[C:11]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]([CH2:35][CH:31]=[CH2:32])([OH:22])[CH2:26][CH:27]=[CH2:28])=[CH:16][CH:17]=2)=[CH:10][S:9][C:8]=1[NH2:25])=[O:6])[CH3:3]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 69607325HCID 69607325, compoundHCID 178418473HCID 178418473, compound

Product 1

HCID 21069288HCID 21069288, compound

Procedure

To a cold (0 C) solution of 2-amino-4-(4-ethoxycarbonylmethoxy-phenyl)-thiophene-3-carboxylic acid ethyl ester hydrochloride salt (1.5 g, 3.90 mmol) in THF (20 mL) was added allylmagnesium chloride (11.7 mL, 23.4 mmol, 2 M solution in THF). The thick slurry was stirred for 0.5 h and was then quenched by the slow addition of saturated NH4Cl (20 mL). The layers were separated, and the aqueous was extracted with EtOAc (3×20 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure to a dark oil. The residue was purified by MPLC (SiO2 gel, 3:1 to 2:1 Hz EtOAc) to give the title compound. MS (ESI) m/e 388 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 0.94 (m, 3H), 2.29 (d, J=7.12 Hz, 4H), 3.70 (m, 2H), 3.96 (q, J=7.12 Hz, 2H), 4.78 (s, 1H), 5.03 (m, 4H), 5.88 (m, 2H), 6.09 (1H), 6.84 (m, 2H), 7.14 (m, 2H), 7.33 (s, 2H).

Workup

  1. customwas then quenched by the slow addition of saturated NH4Cl (20 mL)
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with EtOAc (3×20 mL)
  4. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a dark oil
  7. customThe residue was purified by MPLC (SiO2 gel, 3:1 to 2:1 Hz EtOAc)

Sources & evidence

ORD record
ord-fb2a299e1b0749cfbb2e59c660391c67
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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