Hydrochloric Acid → (S)-2-(Methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid
Reaction equation
[NH2:1][C@@H:2]([CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)[C:3]([OH:5])=[O:4].C(=O)(O)[O-].[Na+].Cl[C:18]([O:20][CH3:21])=[O:19].Cl>>[CH3:21][O:20][C:18]([NH:1][C@@H:2]([CH:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1)[C:3]([OH:5])=[O:4])=[O:19]Participants
5
Procedure
A solution of (S)-amino-(tetrahydro-pyran-4-yl)-acetic acid (200 mg, 1.26 mmol) in saturated aqueous sodium bicarbonate solution (2.46 mL, 25.13 mmol) was stirred until all solids were dissolved. Methyl chloroformate (0.19 mL, 2.51 mmol) was added dropwise, the reaction mixture was stirred for 30 min, and 1N HCl was added to adjust pH to 1. The reaction mixture was extracted with ethyl acetate (3×5 mL) and the organic extracts were dried over sodium sulfate, filtered, concentrated and dried overnight under vacuum to give the title intermediate (248 mg, 91% yield) as a white, sticky solid. (m/z): [M+H]+ calcd for C9H15NO5 218.10. found 218.1.
Workup
- dissolutionwere dissolved
- extractionThe reaction mixture was extracted with ethyl acetate (3×5 mL)
- dry with materialthe organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customdried overnight under vacuum
Sources & evidence
- ORD record
- ord-9bdcbe6284d84b419cfe3c0641863c29
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212168B2
Reaction notes
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