Triethylamine → tert-Butyl (6-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

HRID 1270406Notes

Reaction equation

N[CH:2]([NH:10][C:11]1[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:12]=1C(O)=O)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C>C1(C)C=CC=CC=1>[Br:20][C:18]1[CH:17]=[CH:16][C:12]2[NH:40][C:43](=[O:28])[N:10]([CH2:2][C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[C:11]=2[CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-[(1-Amino-2-tert-butoxy-2-oxoethyl)amino]-4-bromobenzoic acid from Step C (2.72 g, 8.24 mmol), diphenylphosphoryl azide (2.1 mL, 9.9 mmol), and triethylamine (1.4 mL, 9.9 mmol) were dissolved in toluene (80 mL) and heated at 100° C. for 1 h. The cooled mixture was partitioned between EtOAc (200 mL) and water (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=327 (M+1).

Workup

customThe cooled mixture was partitioned between EtOAc (200 mL) and water (100 mL)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by silica gel chromatography
washeluting with a gradient of hexane

Sources & evidence

ORD record: ord-f7783615d34c40889adc1af8c9f100c0
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202251B2

Reaction notes

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