Boc-L-Valine → HCID 67773033, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[F:39][C:40]1([F:45])[CH2:44][CH2:43][NH:42][CH2:41]1>CN(C=O)C>[F:39][C:40]1([F:45])[CH2:44][CH2:43][N:42]([C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:13]([CH3:15])[CH3:14])[CH2:41]1Participants
Conditions
- Temperature
- 0 °C
Procedure
(S)-2-(Tert-butoxycarbonylamino)-3-methylbutanoic acid (1.1 g, 5.06 mmol), which is commercially available, and TBTU (1.63 g, 5.06 mmol) was mixed in DMF (10 mL). The mixture was cooled to 0° C. and TEA (2.105 mL, 15.19 mmol) was added. After 10 min was 3,3-difluoropyrrolidine hydrochloride (0.872 g, 6.08 mmol) added. The resultant mixture was stirred at rt over night. The mixture was concentrated and the residue dissolved in DCM (50 mL). The organic phase was washed with HCl (1M aq. solution, 100 mL), NaHCO3 (saturated, 2×100 mL) and brine (100 mL), filtered through a phase separator and concentrated under reduced pressure to give the title compound (1.54 g, 99%). The obtained crude product was used without further purification. 1H NMR (400 MHz, CD3OD) δ 0.77-1.09, 1.21, 1.43, 1.84-2.08, 2.22-2.69, 3.52-4.40. Total no of protons: 24. LCMS (M+H)+: 307.
Workup
- concentrationThe mixture was concentrated
- dissolutionthe residue dissolved in DCM (50 mL)
- washThe organic phase was washed with HCl (1M aq. solution, 100 mL), NaHCO3 (saturated, 2×100 mL) and brine (100 mL)
- filtrationfiltered through a phase separator
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f07a9b76f88d4604a48d9c76966a59a1
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08361998B2
Reaction notes
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