Hydrochloric Acid → HCID 178452159, compound
Reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:5]=1)(=[O:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1(=O)[O:35][C:33](=[O:34])[C:32]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:31]12.Cl.C1C[O:45][CH2:44]C1>>[C:16]([O:15][C:13]([N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([C:1](=[O:3])[CH:2]=[C:44]([C:32]2([C:33]([OH:35])=[O:34])[CH:31]=[CH:39][CH:38]=[CH:37][CH2:36]2)[OH:45])=[CH:5]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]Participants
6
Procedure
To a solution of 777 mg (3 mmol) of 3-acetyl-1-tert-butoxycarbonyl-indole in THF (10 ml) was added 3.6 ml (3.6 mmol) of 1M LHMDS in THF at −78° C. The mixture was gradually warmed to room temperature. The mixture was cooled again to −78° C. and treated with 525 mg (3.6 mmol) of phthalic anhydride. The reaction solution was warmed to room temperature and mixed with ice water. The solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried, and then concentrated. The obtained residue was crystallized from ethyl acetate-n-hexane to give 362 mg of the titled compound. Yield: 30%.
Workup
- temperatureThe mixture was cooled again to −78° C.
- temperatureThe reaction solution was warmed to room temperature
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- customdried
- concentrationconcentrated
- customThe obtained residue was crystallized from ethyl acetate-n-hexane
Sources & evidence
- ORD record
- ord-d51e272b215c43ca9e07692b3127de85
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06506787B2
Reaction notes
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