Potassium Carbonate → HCID 67809678, compound

HRID 37469Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][CH2:30][N:31]1[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]2[C:32]1=[O:41]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:28][CH2:29][CH2:30][N:31]2[C:35](=[O:36])[C:34]3=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]3[C:32]2=[O:41])=[CH:15][CH:14]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

Conditions

Temperature: 100 °C

Procedure

To 10 ml of anhydrous DMF were added 2.8 g of N- Boc-p-hydroxyphenylglycine methyl ester and 1.38 g (1.0 eq) of anhydrous potassium carbonate, followed by addition of 2.68 g (1.0 eq.) of N-(3-bromopropyl)phthalimide. The mixture was heated at 100° C. for 1 hour. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried. Thereafter, the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent: 5% ethyl acetate/dichloromethane), to give colorless crystals.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materiala saturated aqueous solution of sodium chloride, and dried
distillationThereafter, the solvent was distilled off
customThe residue was purified by silica gel column chromatography (eluent: 5% ethyl acetate/dichloromethane)
customto give colorless crystals

Sources & evidence

ORD record: ord-c28893cc76fc40dea70fc17e3644dafc
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420275

Reaction notes

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