D-Threonine → HCID 86699908, compound
Reaction equation
C([O-])(O)=O.[Na+].[NH2:6][C@@H:7]([C:11]([OH:13])=[O:12])[C@H:8]([CH3:10])[OH:9].Cl[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:16]>C1COCC1.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:9][C@@H:8]([CH3:10])[C@@H:7]([NH:6][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:16])[C:11]([OH:13])=[O:12]Participants
Procedure
In a round bottom flask, NaHCO3 (9.74 g, 116 mmol) was suspended in THF (25 mL) and water (50 mL), then D-threonine (5.47 g, 46.0 mmol) and tetrabutylamonium bromide (0.547 g) were added. n-Octyl chloroformate (10 mL, 51.1 mmol) was added dropwise and the reaction vigorously stirred 18 h at rt. The mixture was then diluted with water, washed twice with Et2O and pH adjusted to 2 with 2M HCl solution. The aqueous phase was extracted with AcOEt, the collected organic phases were dried over Na2SO4, filtered and the solvent removed under vacuum to give the title compound (3.37 g, 27%) as pale yellow oil, which was used in the next step without further purification. Rf=0.26 (Cy/EtOAc 2:8+1% CH3COOH; detection: ninhydrin, bromocresol green). FTIR (cm−1): 3340 (br), 2928, 2856, 1724 (br), 1526, 1261, 1074.
Workup
- customthe reaction vigorously stirred 18 h at rt
- washwashed twice with Et2O
- extractionThe aqueous phase was extracted with AcOEt
- dry with materialthe collected organic phases were dried over Na2SO4
- filtrationfiltered
- customthe solvent removed under vacuum
Sources & evidence
- ORD record
- ord-2926ecfa308443918d70462426876e2d
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353075B2
Reaction notes
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