Ethanethiol → HCID 178471308, compound

HRID 1917604Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([O:19]C)[CH:16]=[CH:17]3)=[C:12]([C:21](=[O:27])[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:11]=2[CH2:28][C:29]([CH3:36])([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(S)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([OH:19])[CH:16]=[CH:17]3)=[C:12]([C:21](=[O:27])[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26])[C:11]=2[CH2:28][C:29]([CH3:35])([CH3:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:9])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(3,3-dimethylbutanoyl)-7-methoxyindolizin-2-yl}-2,2-dimethylpropanoate (310 mg, 0.605 mmol) in CH2Cl2 (5.0 mL) is added aluminum chloride (363 mg, 2.72 mmol). The solution is stirred for 3 h at 23° C. then treated with ethanethiol (0.112 mL, 1.51 mmol) and allowed to stir for 18 h. The mixture is poured into cold 1M aqueous Rochelle's salt solution, extracted with CH2Cl2, washed with brine, dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, hexanes to 1:1 hexanes:EtOAc) gives ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(3,3-dimethylbutanoyl)-7-hydroxyindolizin-2-yl}-2,2-dimethylpropanoate (32 mg, 10%).

Workup

stirringto stir for 18 h
extractionextracted with CH2Cl2
washwashed with brine
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the crude by flash chromatography (SiO2, hexanes to 1:1 hexanes:EtOAc)

Sources & evidence

ORD record: ord-55081b731d844246ab29b0649036b93f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618300B2

Reaction notes

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