Potassium Carbonate → HCID 86714027, compound

HRID 576311Notes

Reaction equation

[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:5]=[C:4]([C@H:19]2[C@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:20]2)[C:3]=1[OH:58].C([O-])([O-])=O.[K+].[K+].Br[CH2:66][CH2:67][CH2:68][OH:69]>CC(C)=O>[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:5]=[C:4]([C@H:19]2[C@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]([O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[O:20]2)[C:3]=1[O:58][CH2:66][CH2:67][CH2:68][OH:69]

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of crude compound 28 (1.33 g, 1.54 mmol) and K2CO3 (0.322 g, 2.31 mmol) in acetone (20 mL) was added 3-bromopropanol (0.30 mL, 2.31 mmol) at r.t. The mixture was stirred at 55° C. for 15 hours. The reaction mixture was cooled to r.t and filtered off to remove inorganic salts. The filtrate was concentrated in vacuo. The residue was purified using normal phase column chromatography to provide the title product 29 (1.47 g, 100%).

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered off
customto remove inorganic salts
concentrationThe filtrate was concentrated in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-db6518d2cafd4bb0bf3a0e7e4c27be96
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034921B2

Reaction notes

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