Hydrochloric Acid → (2S)-2-Amino-3-(tert-butoxy)propanamide hydrochloride
Reaction equation
[NH2:1][C:2](=[O:21])[C@@H:3]([NH:10]C(=O)OCC1C=CC=CC=1)[CH2:4][O:5][C:6]([CH3:9])([CH3:8])[CH3:7].[ClH:22].[H][H]>CO.[Pd]>[ClH:22].[NH2:10][C@@H:3]([CH2:4][O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[C:2]([NH2:1])=[O:21]Participants
6
Procedure
A suspension of Example 31A (784 mg, 2.67 mmol) in methanol (9 mL) at ambient temperature was treated with 10% Pd/C (75 mg) and sufficient 1M HCl to solubilize the substrate (ca. 0.50 mL). The system was equipped with a hydrogen balloon and stirred for 4 hours at ambient temperature. The reaction mixture was purged with nitrogen, filtered through diatomaceous earth (Celite®), rinsed with methanol and water, and the aqueous filtrate was washed with diethyl ether (2×40 mL). The aqueous layer was lyophilized providing 467 mg of the desired product as a white solid.
Workup
- customThe reaction mixture was purged with nitrogen
- filtrationfiltered through diatomaceous earth (Celite®)
- washrinsed with methanol and water
- washthe aqueous filtrate was washed with diethyl ether (2×40 mL)
Sources & evidence
- ORD record
- ord-1a5d4f10c45d4c50a348410a9f1e0075
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06645968B2
Reaction notes
Loading…