Water → HCID 44206680, compound

HRID 1524191Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:20]2[CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][C:26]=3[N:29]3[CH2:34][CH2:33][N:32]([CH2:35][CH3:36])[CH2:31][CH2:30]3)[C:21]2=[O:37])[CH2:12][CH2:13][CH2:14]OS(C)(=O)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CC([O-])(C)C.[Na+].O>COCCOC.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:11]2[N:20]3[C:21](=[O:37])[C:22]4[C:27]([C@H:28]3[CH2:14][CH2:13][CH2:12]2)=[C:26]([N:29]2[CH2:30][CH2:31][N:32]([CH2:35][CH3:36])[CH2:33][CH2:34]2)[CH:25]=[CH:24][CH:23]=4)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 60 °C

Procedure

Methanesulfonic acid 4-(3,4-dimethoxy-phenyl)-4-[4-(4-ethyl-piperazin-1-yl)-1-oxo-1,3-dihydro-isoindol-2-yl]-butyl ester (112 mg, 0.211 mmol) was dissolved in DME (0.80 mL), and a 4 M solution of NaOtBu in THF (0.5 mL) was added. The resulting mixture was stirred at 60° C. for 1 hour and then allowed to cool to room temperature. The resulting mixture was then poured into water (10 mL) and extracted with EtOAc (2 times, 15 mL). The organic layers were combined, washed with brine (10 mL), dried over Na2SO4, and concentrated in vacuum to yield a residue. The residue was purified using prep-HPLC 5-90 gradient water (0.2% TFA buffer)/acetonitrile (0.15% TFA buffer) to yield the title compound as a pale yellow solid.

Workup

temperatureto cool to room temperature
extractionextracted with EtOAc (2 times, 15 mL)
washwashed with brine (10 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuum
customto yield a residue
customThe residue was purified

Sources & evidence

ORD record: ord-89f972db625e43a29bf62dd952698867
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079896B2

Reaction notes

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