Benzyl Bromide → HCID 68825250, compound

HRID 1272429Notes

Reaction equation

HRID 1272429 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:32])=[C:8]([S:10]([NH:13][CH2:14][CH2:15][C:16]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][C:17]=2[O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:12])=[O:11])[CH:9]=1)(=[NH:3])N.C([N:36](CC)C(C)C)(C)C.[CH2:42](Br)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[CH3:50][C:51]([CH3:70])([CH3:69])[C:52]([O:54][CH2:55][O:56][C:57](OC1C=CC([N+]([O-])=O)=CC=1)=[O:58])=O.[Cl-].[Na+].[OH2:73]>CN(C)C=O.O>[CH3:50][C:51]([CH3:70])([CH3:69])[C:52]([O:54][CH:55]([NH2:36])[O:56][C:57](=[O:58])[N:3]=[CH:1][C:4]1[CH:5]=[CH:6][C:7]([O:32][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[C:8]([S:10](=[O:12])(=[O:11])[NH:13][CH2:14][CH2:15][C:16]2[CH:28]=[CH:27][C:26]([CH:29]([CH3:30])[CH3:31])=[CH:25][C:17]=2[O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=1)=[O:73]

Participants

8

Reactant 5

HCID 7498Benzyl BromideHCID 81531Diisopropylethylamine2×HCID 15053081HCID 15053081, compoundHCID 57417360Sodium chloride; waterHCID 136375592HCID 136375592, compound

Product 1

HCID 68825250HCID 68825250, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 131 mg of ethyl [2-[2-(5-carbamimidoyl-2-hydroxybenzenesulfonylamino)ethyl]-5-isopropylphenoxy]-acetate in 5 mL of N,N-dimethylformamide was added 0.91 mL of N,N-diisopropylethylamine. To the stirred mixture was added 0.069 mL of benzyl bromide at 40° C., and the mixture was stirred at room temperature over night. To the reaction mixture were added 0.91 mL of N,N-diisopropylethylamine and 86 mg of 4-nitrophenoxycarbonyloxymethyl 2,2-dimethylpropionate, and the mixture was stirred at room temperature for 6 hours. To the reaction mixture were added 10 mL of water and 10 mL of brine, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 99 mg of amino-[4-benzyloxy-3-[[2-[4-isopropyl-2-(ethoxycarbonylmethoxy)phenyl]-ethyl]sulfamoyl]phenyl]methylenecarbamoyloxymethyl 2,2-dimethylpropionate.

Workup

  1. stirringthe mixture was stirred at room temperature for 6 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ee234dabfb0541ffbea58d080c27a82e
Source dataset
uspto-grants-2007_04
Patent number
US07208524B2

Reaction notes

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