Water → HCID 68937610, compound

HRID 1260979Notes

Reaction equation

[C:1]([N:5]1[CH2:10][CH2:9][C@@H:8]([N:11]([CH3:21])[C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C@H:7]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:6]1)(=[O:4])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[NH:36]1[CH2:40][CH2:39][CH2:38][C:37]1=[O:41].O>CN(C=O)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]([N:11]([C@@H:8]2[CH2:9][CH2:10][N:5]([C:1](=[O:4])[CH2:2][CH2:3][N:36]3[CH2:40][CH2:39][CH2:38][C:37]3=[O:41])[CH2:6][C@H:7]2[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH3:21])=[O:20])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of the compound obtained in Example 588 (0.050 mg) in DMF (1 mL) were added potassium carbonate (0.0166 mg) and 2-pyrrolidinone (0.0093 mL), and the mixture was stirred at 110° C. for 1 hr. To the reaction mixture was added water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 30→100% ethyl acetate/hexane) to give the title compound (37 mg, 63%) as a white powder.

Workup

extractionthe resultant product was extracted with ethyl acetate
washThe organic layer was washed with brine
customdried
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (NH Chromatorex) (solvent gradient; 30→100% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-d778c06c181c4051ad034d6c4efa7e31
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470816B2

Reaction notes

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