Cesium carbonate → HCID 59437434, compound

HRID 1512209Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1/[CH:24]=[CH:25]/[CH:26]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]([O:49][CH3:50])=[O:48])=[CH:43][CH:42]=1)[CH2:27][CH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1>CN(C=O)C>[CH3:50][O:49][C:47]([C:44]1[CH:43]=[CH:42][C:41]([CH2:40][CH2:39][CH:26](/[CH:25]=[CH:24]/[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][CH2:2][CH2:3][CH2:4][N:5]2[CH2:9][CH2:8][CH2:7][C:6]2=[O:10])[CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][CH:38]=2)=[CH:46][CH:45]=1)=[O:48]

Participants

Conditions

Temperature: 60 °C

Procedure

119 mg (0.74 mmol) of 1-(3-chloropropyl)pyrrolidin-2-one [CAS Reg. No. 91152-30-6] and 240 mg (0.74 mmol) of anhydrous cesium carbonate are added to a solution of 169 mg (0.37 mmol) of methyl 4-[(4E)-5-(2-hydroxyphenyl)-3-{2-[4-(methoxycarbonyl)phenyl]ethyl}pent-4-en-1-yl]benzoate in 2.5 ml of dry DMF, and the mixture is then stirred at 60° C. for 12 h. The mixture is then filtered, and the filtrate is evaporated to dryness. The residue is purified by preparative HPLC. This gives 169 mg (purity 94%, 0.27 mmol, 74% of theory) of a colorless oil.

Workup

filtrationThe mixture is then filtered
customthe filtrate is evaporated to dryness
customThe residue is purified by preparative HPLC

Sources & evidence

ORD record: ord-a5b395a9e1534463914639df75c262af
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217063B2

Reaction notes

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