Water → HCID 23001825, compound

HRID 398082Notes

Reaction equation

HRID 398082 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([O:10][C:11]3[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([NH2:21])=[O:20])=[CH:13][C:12]=3[CH2:22][N:23]([CH3:25])[CH3:24])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.O>C1COCC1>[S:1]1[C:5]2[CH:6]=[C:7]([O:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][C:19]([NH2:21])=[O:20])=[CH:13][C:12]=3[CH2:22][N:23]([CH3:25])[CH3:24])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 962WaterHCID 23001839HCID 23001839, compound

Product 1

HCID 23001825HCID 23001825, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Sml2 in THF (0.1 M, 21.9 mL, 2.19 mmol) was added to a solution of the alkene of Example 50 (194 mg, 0.55 mmol) in THF (5 mL) under nitrogen followed by water (1 mL). After stirring at room temperature for 10 min the reaction was quenched with 6M NaOH (10 mL) and stirred for 30 min. The organic phase was separated and the aqueous phase was extracted with EtOAc (2×20 mL). The combined organic layers were dried (MgSO4) and evaporated to an oil, which was purified by column chromatography [SiO2; 93:7:1 (DCM/MeOH/880 NH3) increasing polarity to 90:10:1] to give the title compound (90 mg, 46%); δH (CDCl3, 400 MHz) 2.25 (6H, s), 2.54 (2H, t), 2.97 (2H, t), 3.22 (2H, t), 3.36 (2H, t), 3.42 (2H, s), 5.20-5.46 (2H, br), 6.54 (1H, d), 6.73 (1H, s), 6.81 (1H, d), 7.05 (2H, m), 7.31 (1H, s); MS m/z (TS+) 357 (MH+).

Workup

  1. customwas quenched with 6M NaOH (10 mL)
  2. stirringstirred for 30 min
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with EtOAc (2×20 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customevaporated to an oil, which
  7. customwas purified by column chromatography [SiO2; 93:7:1 (DCM/MeOH/880 NH3) increasing polarity to 90:10:1]

Sources & evidence

ORD record
ord-ce2c70d3fc2441a496eef278db6385f2
Source dataset
uspto-grants-2003_08
Patent number
US06610747B2

Reaction notes

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