Potassium Sodium Tartrate → HCID 58505640, compound

HRID 1917607Notes

Reaction equation

C([O:5][C:6]1[CH:14]=[CH:13][C:12]2[N:8]([C:9]([C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[C:10]([CH2:24][C:25]([CH3:32])([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:11]=2[C:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[O:16])[CH:7]=1)(C)(C)C.[Cl-].[Al+3].[Cl-].[Cl-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]([C:11]2[C:10]([CH2:24][C:25]([CH3:31])([CH3:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:9]([C:33](=[O:38])[C:34]([CH3:36])([CH3:37])[CH3:35])[N:8]3[C:12]=2[CH:13]=[CH:14][C:6]([OH:5])=[CH:7]3)=[O:16])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of the ethyl 3-{6-tert-butoxy-1-[(4-chlorophenyl)carbonyl]-3-(2,2-dimethylpropanoyl)indolizin-2-yl}-2,2-dimethylpropanoate (1.23 g, 2.27 mmol) in CH2Cl2 (10 mL) is added aluminum chloride (454 mg, 3.41 mmol). The reaction is stirred for 30 min at 23° C. then treated with a saturated aqueous solution of Rochelle's salt. The mixture is partitioned between CH2Cl2 and brine, then organics are collected, dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, hexanes to 25% EtOAc in hexanes) affords ethyl 3-{1-[(4-chlorophenyl)carbonyl]-3-(2,2-dimethylpropanoyl)-6-hydroxyindolizin-2-yl}-2,2-dimethylpropanoate (605 mg, 22%).

Workup

customThe mixture is partitioned between CH2Cl2 and brine
customorganics are collected
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the crude by flash chromatography (SiO2, hexanes to 25% EtOAc in hexanes)

Sources & evidence

ORD record: ord-840aa56336c7425dbfca90aa28c89491
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618300B2

Reaction notes

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