Hydrochloric Acid → ((2S)-2-amino-3-methylbutyl)carbamic acid p-nitrobenzyl ester hydrochloride
Reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][O:9][C:10](=[O:25])[NH:11][CH2:12][C@@H:13]([NH:17]C(OC(C)(C)C)=O)[CH:14]([CH3:16])[CH3:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].[ClH:28]>O1CCOCC1>[ClH:28].[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][O:9][C:10](=[O:25])[NH:11][CH2:12][C@@H:13]([NH2:17])[CH:14]([CH3:15])[CH3:16])=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
4
Procedure
To a solution of ((2S)-2-t-butoxycarbonylamino-3-methylbutyl)-carbamic acid p-nitrobenzyl ester (3.13 g, 8.21 mmol) (obtained as described in Reference Example 61(3)) in 1,4-dioxane (31 ml) was added a 4N solution of hydrogen chloride in 1,4-dioxane (31 ml) in an ice bath, and the mixture was stirred at room temperature for 4 hours. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the resulting mixture was filtered off and washed with ethyl acetate to give ((2S)-2-amino-3-methylbutyl)carbamic acid p-nitrobenzyl ester hydrochloride (1.82 g, yield 70%) as pale yellow crystals.
Workup
- customthe completion of the reaction
- concentrationthe reaction mixture was concentrated under reduced pressure
- additionEthyl acetate was added to the residue
- filtrationthe resulting mixture was filtered off
- washwashed with ethyl acetate
Sources & evidence
- ORD record
- ord-58203e05c0824c04a2f5576a5da5ae0f
- Source dataset
- uspto-grants-2006_02
- Patent number
- US07001897B2
Reaction notes
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