4-Methylmorpholine → HCID 67772960, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:13]1[CH2:15][CH2:14]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:17]1[CH2:22][CH2:21]OC[CH2:18]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N1CCC1>CN(C=O)C>[N:17]1([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]2[CH2:15][CH2:14]2)[CH2:18][CH2:21][CH2:22]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(S)-2-(Tert-butoxycarbonylamino)-2-cyclopropylacetic acid (2.0 g, 9.30 mmol), which is commercially available, and NMM (3.07 mL, 27.9 mmol) was mixed in DMF (20 mL). The mixture was cooled to 0° C. and TBTU (3.34 g, 10.42 mmol) was added. After 10 min at rt was azetidine (1.6 mL, 23.7 mmol) added. The resultant mixture was stirred at rt over night. The mixture was concentrated and the residue dissolved in DCM (300 mL). The organic phase was washed with NaHCO3 (saturated, 150 mL) and brine (150 mL), filtered through a phase separator and concentrated under reduced pressure to give the title compound (2.04 g, 86%). The obtained crude product was used without further purification. 1H NMR (400 MHz, CD3OD) δ 0.39, 0.44-0.63, 1.09, 1.43, 2.31, 3.84, 3.93-4.46, 5.30. Total no of protons: 22.
Workup
- concentrationThe mixture was concentrated
- dissolutionthe residue dissolved in DCM (300 mL)
- washThe organic phase was washed with NaHCO3 (saturated, 150 mL) and brine (150 mL)
- filtrationfiltered through a phase separator
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e3d47ccf14b54bc386b17e3b9ea6c267
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08361998B2
Reaction notes
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