Trifluoroacetic acid → HCID 178517216, compound

HRID 642166Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.C(O)(C(F)(F)F)=O.[CH2:20]([C@H:27]([O:38][C:39]1[CH:55]=[CH:54][C:42]([C:43]([NH:45][NH:46]C(OC(C)(C)C)=O)=[O:44])=[CH:41][CH:40]=1)[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N:46][NH:45][C:43]([C:42]1[CH:54]=[CH:55][C:39]([O:38][C@@H:27]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=[CH:40][CH:41]=1)=[O:44]

Participants

Conditions

Temperature: 100 °C

Procedure

Following the general method as outlined in Example 1, into a suspension of 5-iodo-1H-indole-2,3-dione in acetic acid in the presence of 5% TFA was added tert-butyl 2-{4-[(1S)-1-benzyl-2-(benzyloxy)-2-oxoethoxy]benzoyl}hydrazinecarboxylate. After stirring at 100° C., the reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 60° C. for 15 hrs gave 164 mg of the title compound (76%) as a yellow solid in 98.8% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

temperaturethe reaction mixture was cooled to rt
customa yellow solid precipitated out
filtrationFiltration on a fritté
washwashing with AcOH, water
customdrying under vacuo at 60° C. for 15 hrs

Sources & evidence

ORD record: ord-1e5f184865b343758e94355c33631c8c
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696231B2

Reaction notes

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