Triethylamine → HCID 22476037, compound
Reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1.CCN(CC)CC.[O:19](C(OC(C)(C)C)=O)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O.Cl.O.P>CN(C=O)C>[C:23]([O:22][C:20]([N:7]([CH:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)[CH2:8][C:9]([OH:11])=[O:10])=[O:19])([CH3:26])([CH3:25])[CH3:24]Participants
7
Conditions
- Temperature
- 60 °C
Procedure
2-(tetrahydro-2H-pyran-4-ylamino)acetic acid (0.2 g, 1.256 mmol) F44 was dissolved in DMF (22.5 mL) and Et3N (2.5 mL, 17.94 mmol). After 5 minutes BOC2O (0.583 mL, 2.51 mmol) was added and the reaction solution was heated to 60° C. for 1 h. The reaction was concentrated by reduced pressure providing a light yellow oil to which was added 20 mL HCl/H2O which was adjusted to PH3 at 0° C. and stirred for 10 minutes. The reaction mixture was extracted by ethyl acetate 3×20 mL, dried (MgSO4), filtered, and concentrated to dryness. Ether was added and the mixture was sonicated and filtered providing a white solid F45 2-(tert-butoxycarbonyl(tetrahydro-2H-pyran-4-yl)amino)acetic acid (0.14 g, 0.540 mmol, 43.0% yield).
Workup
- concentrationThe reaction was concentrated by reduced pressure
- customproviding a light yellow oil to which
- extractionThe reaction mixture was extracted by ethyl acetate 3×20 mL
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated to dryness
- additionEther was added
- customthe mixture was sonicated
- filtrationfiltered
Sources & evidence
- ORD record
- ord-34f9b4ba363a485c8b439229d8ff7386
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642025B2
Reaction notes
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