Hydrochloric Acid → (S)-2-(tert-butoxycarbonylamino)-3-(4-chlorobutanamido)propanoic acid
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][NH2:11].Cl>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[C:18]([O:17][C:15]([NH:8][C@@H:9]([CH2:10][NH:11][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])[C:12]([OH:14])=[O:13])=[O:16])([CH3:21])([CH3:20])[CH3:19]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
4-Chlorobutanoyl chloride (12.1 g, 86 mmol) was added to a solution of Boc-L-Dap (16.0 g, 78 mmol) in dioxane (160 mL) and 10% aqueous Na2CO3 (180 mL) at 0° C. dropwise. The reaction mixture was stirred at 0° C. for 1 h and then allowed to warm to ambient temperature and stirred overnight. The mixture was acidified with 1N aqueous hydrochloric acid to pH=3 and extracted with EtOAc (300 mL×3). The combined organic phases were washed with 1N aqueous hydrochloric acid (300 mL×3) and brine (300 mL×1), dried over anhydrous sodium sulfate, and concentrated to afford (S)-2-(tert-butoxycarbonylamino)-3-(4-chlorobutanamido)propanoic acid (15.5 g, 64% yield), which was used directly without further purification.
Workup
- temperatureto warm to ambient temperature
- stirringstirred overnight
- extractionextracted with EtOAc (300 mL×3)
- washThe combined organic phases were washed with 1N aqueous hydrochloric acid (300 mL×3) and brine (300 mL×1)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8d72f0c3ca4c40a4a38d5aa1be72d397
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434761B2
Reaction notes
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