Reaction equation
C(=O)([O-])O.[Na+].O1CCCC1.[NH2:11][CH2:12][C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14].[CH3:20][C@@H:21]([C@@H:28]1[C@@:32]2([CH3:50])[CH2:33][CH2:34][CH:35]3[C@@:40]4([CH3:49])[CH2:41][CH2:42][CH:43]([O:45][C:46](Cl)=[O:47])[CH2:44][C:39]4=[CH:38][CH2:37][CH:36]3[CH:31]2[CH2:30][CH2:29]1)[CH2:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26]>O>[CH3:27][CH:25]([CH2:24][CH2:23][CH2:22][C@H:21]([C@@H:28]1[C@:32]2([CH3:50])[C@H:31]([C@H:36]3[C@H:35]([CH2:34][CH2:33]2)[C@:40]2([CH3:49])[C:39]([CH2:44][C@@H:43]([O:45][C:46]([NH:11][CH2:12][C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])=[O:47])[CH2:42][CH2:41]2)=[CH:38][CH2:37]3)[CH2:30][CH2:29]1)[CH3:20])[CH3:26]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium hydrogencarbonate (0.168 g) and tetrahydrofuran (20 ml) were added to a suspension of glycylglycine (0.15 g) in water (20 ml). After tetrahydrofuran (20 ml) and cholesteryl chloroformate (0.898 g) were added to the resulting transparent solution at 0° C., the mixture was stirred for an hour. The reaction mixture was concentrated under reduced pressure and, methanl (10 ml) and chloroform (10 ml) were added to the residue. By filtration, the transparent solution was obtained. The solvent was distilled off to give crude crystals (0.98 g). The crude crystals were then purified by silica gel chromatography to give N-(cholest-5-ene-3β-oxycarbonyl)glycylglycine (0.5 g) as white powders.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure and, methanl (10 ml) and chloroform (10 ml)
- additionwere added to the residue
- filtrationBy filtration
- customthe transparent solution was obtained
- distillationThe solvent was distilled off
- customto give crude crystals (0.98 g)
- customThe crude crystals were then purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-c01942f2ad344ee7b3deac1007c75775
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05152999
Linked notes
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