Hydrochloric Acid → HCID 16114999, compound
Reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:24][CH2:25][O:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:9]1[C:10]([N+:21]([O-:23])=[O:22])=[CH:11][C:12]([N+:18]([O-:20])=[O:19])=[C:13]([CH:17]=1)[C:14](O)=[O:15])(=[O:4])=[O:3].[NH2:31][CH2:32][CH:33]([OH:36])[CH2:34][OH:35].Cl>>[CH3:1][S:2]([O:5][CH2:6][CH2:7][N:8]([CH2:24][CH2:25][O:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:9]1[CH:17]=[C:13]([C:14]([NH:31][CH2:32][CH:33]([OH:36])[CH2:34][OH:35])=[O:15])[C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22])(=[O:3])=[O:4]Participants
Procedure
Reaction of the crude acid chloride made as above from acid 8 (2.9 g, 6.15 mmol) was dissolved in Me2CO (100 mL), cooled in an ice-bath and treated with an excess of 3-amino-1,2-propanediol. After string for 10 min. the reaction mixture was acidified to pH 2-3 with 1 N HCl, most of the solvent was evaporated, and the residue was partitioned between water and EtOAc. The aqueous layer was re-extracted with EtOAc and the combined organic phases were dried and evaporated. The residue was adsorbed directly onto silica gel and chromatographed, elution with EtOAc/MeOH (from 50:1 to 10:1) giving 2-(5-{[(2,3-dihydroxypropyl)amino]carbonyl}{2-[(methylsulfonyl)oxy]ethyl}-2,4-dinitroanilino)ethyl methanesulfonate (9c) (2.92 g, 87%) as a yellow oil;
Workup
- dissolutionwas dissolved in Me2CO (100 mL)
- temperaturecooled in an ice-bath
- customwas evaporated
- customthe residue was partitioned between water and EtOAc
- extractionThe aqueous layer was re-extracted with EtOAc
- customthe combined organic phases were dried
- customevaporated
- customchromatographed
- washelution with EtOAc/MeOH (from 50:1 to 10:1)
Sources & evidence
- ORD record
- ord-e3039f11af164e4dac22ae3921fcf770
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776924B2
Reaction notes
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