Succinic anhydride → N-(5-[2-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-propyl}-benzo[1,3]dioxol-2-ylmethyl)-succinamic acid

HRID 2099716Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[O:7][C:6]2[CH:8]=[CH:9][C:10]([CH2:12][CH:13]([N:15]([CH2:22][CH3:23])[C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH3:14])=[CH:11][C:5]=2[O:4]1.[C:24]1(=[O:30])[O:29][C:27](=[O:28])[CH2:26][CH2:25]1.C(N(CC)CC)C>ClCCCl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH2:22]([N:15]([C:16](=[O:21])[C:17]([F:18])([F:20])[F:19])[CH:13]([CH3:14])[CH2:12][C:10]1[CH:9]=[CH:8][C:6]2[O:7][CH:3]([CH2:2][NH:1][C:24](=[O:30])[CH2:25][CH2:26][C:27]([OH:29])=[O:28])[O:4][C:5]=2[CH:11]=1)[CH3:23]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 558 mg (1.67 mmol) of 2J in 25 mL of 1,2 dichloroethane was added 435 mg (4.34 mmol) of succinic anhydride, 280 μL (2 mmol) of triethylamine and 112 mg (0.91 mmol) of 4-DMAP. The reaction mixture was allowed to stir at 40° C. under argon atmosphere for 2.5 hours. It was then diluted with 50 mL of ethyl acetate and washed with 3×30 mL of 5% ammonium chloride solution. The organic layer was dried (anhydrous Na2SO4) and concentrated under reduced pressure to dryness. The residue was purified by silica gel column chromatography to give 629 mg (1.45 mmol, 86%) of 2K as a colorless gum (M+H, 433).

Workup

washwashed with 3×30 mL of 5% ammonium chloride solution
dry with materialThe organic layer was dried (anhydrous Na2SO4)
concentrationconcentrated under reduced pressure to dryness
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-f61122a57b614950add88c4c8d630c84
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569676B2

Reaction notes

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