Lithium Chloride → Anzemet

HRID 20204Notes

Reaction equation

COC([CH:5]1[C:14](=[O:15])[CH:13]2[CH2:16][CH:7]3[CH2:8][CH:9]([O:17][C:18]([C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[NH:22][CH:21]=4)=[O:19])[CH2:10][CH:11]([CH2:12]2)[N:6]13)=O.[Li+].[Cl-].CCOC(C)=O.CO>CN(C)C=O>[O:15]=[C:14]1[CH:13]2[CH2:16][CH:7]3[CH2:8][CH:9]([O:17][C:18]([C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[NH:22][CH:21]=4)=[O:19])[CH2:10][CH:11]([CH2:12]2)[N:6]3[CH2:5]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 3.1 gr (8.1 mmol) of 5-(1H-Indole-3-carbonyloxy)-10-oxo-8-aza-tricyclo[5.3.1.03,8]undecane-9-carboxylic acid methyl ester and LiCl (0.69 gr, 16.23 mmol) in dimethylformamide (90 mL) is heated to 140° C. Once 4 hours have elapsed, and after checking by thin-layer chromatography (AcOEt/MeOH 9:1) that the reaction has been completed, the mixture is left to cool. Volatile substances are evaporated at low pressure and the residue is dissolved in dichloromethane (150 mL). This is washed with a saturated aqueous solution of NaCl (70 mL), and the organic phase is dried over magnesium sulphate and evaporated, to provide crude 1H-Indole-3-carboxylic acid 10-oxo-8-aza-tricyclo[5.3.1.03,8]undec-5-yl ester as a solid (2.18 gr, 83%).

Workup

customOnce 4 hours
waitthe mixture is left
temperatureto cool
customVolatile substances are evaporated at low pressure
dissolutionthe residue is dissolved in dichloromethane (150 mL)
washThis is washed with a saturated aqueous solution of NaCl (70 mL)
dry with materialthe organic phase is dried over magnesium sulphate
customevaporated

Sources & evidence

ORD record: ord-889f3a8880784feb9fedf8b812d840f5
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745628B2

Reaction notes

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