4-Bromophthalic anhydride → HCID 54236903, compound

HRID 393477Notes

Reaction equation

HRID 393477 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[Br:22][C:23]1[CH:24]=[C:25]2[C:30](=O)[O:29][C:27](=[O:28])[C:26]2=[CH:32][CH:33]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>ClCCl.O>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:30](=[O:29])[C:25]3[C:26](=[CH:32][CH:33]=[C:23]([Br:22])[CH:24]=3)[C:27]2=[O:28])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

6

Reactant 3

HCID 665904-Bromophthalic anhydrideHCID 682631,1'-CarbonyldiimidazoleHCID 110118554-Amino-N-((1,1-dimethylethoxy)carbonyl)-L-phenylalanine methyl ester

Product 1

HCID 54236903HCID 54236903, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-amino-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester (6.78 mmol, 1.99 g) in dichloromethane (90 mL) was added a solution of 4-bromophthalic anhydride (6.78 mmol, 1.54 g) in dichloromethane (30 mL) and 1,1′-carbonyldiimidazole (6.78 mmol, 1.1 g) at room temperature. The resulting solution was stirred for 15 h at which time TLC analysis of the mixture indicated the absence of starting material. The mixture was diluted with water (100 mL) and layers were separated. The aqueous layer was extracted with dichloromethane (2×100 mL) and the combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum gave a crude product which was purified by silica gel column chromatography to obtaine 2.4 g (70%) of a white solid: mp 168-170° C. HR MS C23H23BrN2O6): Obs mass, 525.0656. Calcd mass, 525.0637 (M+Na).

Workup

  1. customwere separated
  2. extractionThe aqueous layer was extracted with dichloromethane (2×100 mL)
  3. washthe combined extracts were washed with brine solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration of the drying agent and concentration of the solvent under vacuum

Sources & evidence

ORD record
ord-9a5ee6928f774f4d8bf878e1f1dd6e6d
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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