Dimethylformamide → HCID 86608945, compound

HRID 1985727Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:24]2[CH2:26][CH2:25]2)=[C:14](Br)[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.CN(C)[CH:42]=[O:43]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:24]2[CH2:26][CH2:25]2)=[C:14]([CH:42]=[O:43])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.847 g (4R,9aR)-7-bromo-6-[(tert-butoxycarbonyl-cyclopropyl-amino)-methyl]-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 30 ml toluene was added at −78° C. 1.5 ml of a 1.5M solution of tert-butyllithium and the mixture was stirred at this temperature for 10 min. To the resulting mixture was added 2.00 ml dimethylformamide and the mixture was stirred at −78° C. for 1 h and at 0° C. for 30 min. The reaction was quenched by addition of 10% aqueous citric acid. The phases were separated and the organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=1:1 to yield 0.200 g of the title compound as orange yellow solid. (MS: 487.3 (M+H+)).

Workup

customThe reaction was quenched by addition of 10% aqueous citric acid
customThe phases were separated
customthe organic phase was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record: ord-8cebece94cea43b7ba27a017fe68a9f2
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547699B2

Reaction notes

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