Water → HCID 131728515, compound

HRID 1172549Notes

Reaction equation

HRID 1172549 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[OH-].[Na+].C[O:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[CH2:17][S:16](=[O:26])(=[O:25])[C:15]=2[CH:27]=1)=[O:10].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[CH2:1]([N:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[CH2:17][S:16](=[O:25])(=[O:26])[C:15]2[CH:27]=[C:11]([C:9]([OH:10])=[O:8])[CH:12]=[CH:13][C:14]1=2)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 131728514HCID 131728514, compound

Product 1

HCID 131728515HCID 131728515, compoundYield 13.41%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent

Procedure

Allyl bromide (0.042 mL, 0.49 mmol), tetrabutylammonium hydrogen sulphate (0.033 g, 0.099 mmol) and 25% aqueous sodium hydroxide (0.5 mL) were added to a solution of Example 166e (0.1 g, 0.33 mmol) in benzene (2 mL). The reaction mixture was stirred for 7 h at room temperature, treated with water and extracted with ethyl acetate. The organic extract was washed with water, 10% aqueous HCl, dried, concentrated and subjected to hydrolysis as described in Example 1i to obtain the title compound. Yield: 13.41%; 1H NMR (DMSO-d6): δ 4.50 (d, 2H, CH2), 5.00 (s, 2H, CH2), 5.30 (d, 2H, CH2), 5.80 (m, 1H, CH), 7.30-7.60 (m, 5H, Ar), 8.10 (d, 1H, Ar), 8.20 (s, 1H, Ar); MS: m/e (ES+) 330 (M+).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water, 10% aqueous HCl
  4. customdried
  5. concentrationconcentrated
  6. customsubjected to hydrolysis

Sources & evidence

ORD record
ord-b4f84dbe2313405f88d7b1c5fcadc5ab
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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