Tetrahydrofuran → 3-{[(1R)-Isobutanoyloxyisobutoxy]carbonylamino}propyl Phosphonous Acid
Reaction equation
[CH3:1][CH:2]([CH3:39])[C:3]([O:5][C@H:6]([O:10][C:11]([O:13]N1C(=O)[C@@H](OC(=O)C2C=CC=CC=2)[C@H](OC(=O)C2C=CC=CC=2)C1=O)=O)[CH:7]([CH3:9])[CH3:8])=[O:4].[NH2:40][CH2:41][CH2:42][CH2:43][P:44]([OH:46])[OH:45].C1COCC1>O>[C:3]([O:5][C@H:6]([O:10][C:11]([NH:40][CH2:41][CH2:42][CH2:43][P:44]([OH:46])[OH:45])=[O:13])[CH:7]([CH3:8])[CH3:9])(=[O:4])[CH:2]([CH3:1])[CH3:39]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 19 °C
Procedure
To a 3 L three necked round bottom flask fitted with a mechanical stirrer, temperature probe, and nitrogen inlet is added (25) (100 mmol), 3-aminopropylphosphonous acid (100 mmol), THF (1 L), and water (100 mL). The suspension is stirred under a nitrogen atmosphere at 18-20° C. for 4 h during which time the reaction mixture becomes homogeneous. The THF is removed in vacuo and the reaction mixture is diluted with methyl tert-butyl ether (250 mL) and washed with 1N HCl (1×500 mL) and water (2×200 mL). The organic phase is separated and concentrated in vacuo to leave a white solid. The solid is purified by flash chromatography to afford the title compound (39) as a white solid.
Workup
- customThe THF is removed in vacuo
- additionthe reaction mixture is diluted with methyl tert-butyl ether (250 mL)
- washwashed with 1N HCl (1×500 mL) and water (2×200 mL)
- customThe organic phase is separated
- concentrationconcentrated in vacuo
- customto leave a white solid
- customThe solid is purified by flash chromatography
Sources & evidence
- ORD record
- ord-f1050bbccc3740fcb904256f04b97391
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935686B2
Reaction notes
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