Acetic Acid → 2-(6-(5-Methyl-3-oxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-1H-indol-1-yl)acetic acid

HRID 453868Notes

Reaction equation

[H-].[Na+].C([O:7][C:8](=[O:34])[CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][CH2:20][C:21]3[N:22]([C:27](OC(C)(C)C)=[O:28])[C:23]([CH3:26])=[CH:24][CH:25]=3)[CH:17]=2)[CH:12]=[CH:11]1)(C)(C)C.O.C(O)(=O)C>C1COCC1.C(OCC)(=O)C>[CH3:26][C:23]1[N:22]2[C:27](=[O:28])[N:19]([C:16]3[CH:17]=[C:18]4[C:13]([CH:12]=[CH:11][N:10]4[CH2:9][C:8]([OH:7])=[O:34])=[CH:14][CH:15]=3)[CH2:20][C:21]2=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 25 °C

Procedure

NaH (2.0 equiv., 60% in mineral oil) was suspended at 0° C. in THF (6 ml). A solution of tert-butyl 2-((1-(2-tert-butoxy-2-oxoethyl)-1H-indol-6-ylamino)methyl)-5-methyl-1H-pyrrole-1-carboxylate (0.797 mmol, 1.0 equiv.) in THF (2 ml) was added, and the mixture was stirred for 14 h at 25° C. The reaction mixture was hydrolysed with water (50 ml) and diluted with ethyl acetate (100 ml). The aqueous phase was adjusted to an acidic pH value with acetic acid and extracted with ethyl acetate (2×50 ml). The combined organic phases were dried over Na2SO4 and concentrated under reduced pressure. The product was crystallized from the residue with hexane. Yield: 81%

Workup

extractionextracted with ethyl acetate (2×50 ml)
dry with materialThe combined organic phases were dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe product was crystallized from the residue with hexane

Sources & evidence

ORD record: ord-dcc72858a3b6465fb9d984520f8aab50
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492559B2

Reaction notes

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