Ammonium → HCID 11369963, compound
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH2:10][C:11](O)=[O:12])=[CH:5][C:4]=1[C:18]([F:21])([F:20])[F:19])#[N:2].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[N:37]1C=CC=CC=1.[NH4+]>C(#N)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH2:10][C:11]([NH2:37])=[O:12])=[CH:5][C:4]=1[C:18]([F:21])([F:20])[F:19])#[N:2]Participants
Procedure
A mixture of N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycine (0.298 g, 1 mmol), di-tert-butyl dicarbonate (0.436 g, 2 mmol), pyridine (0.100 g, 1.25 mmol), and ammonium hydrocarbonate (0.160 g, 2.25 mmol) was stirred for 24 h in acetonitrile (8 mL). The solvent was removed under reduced pressure, then water (10 mL) was added to the residue. The resulting solid was filtered, washed with water (3×5 mL), and then dried. After drying, the solid was suspended in diethyl ether (10 mL) and stirred for 12 h. The mixture was filtered, washed with diethyl ether (5 mL), and dried to obtain 0.118 g (40%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.63 (d, J=8.6 Hz, 1H), 7.03 (d, J=2.3 Hz, 1H), 6.84 (dd, J=8.8, 2.5 Hz, 1H), 6.02 (bs, 1H), 5.57 (bs, 1H), 4.10 (s, 2H), 3.38 (d, J=6.6 Hz, 2H), 1.08 (m, 1H), 0.67 (m, 2H), 0.33 (m, 2H).
Workup
- customThe solvent was removed under reduced pressure
- additionwater (10 mL) was added to the residue
- filtrationThe resulting solid was filtered
- washwashed with water (3×5 mL)
- customdried
- customAfter drying
- filtrationThe mixture was filtered
- washwashed with diethyl ether (5 mL)
- customdried
Sources & evidence
- ORD record
- ord-d593c938c25047819e526f532d52d981
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514470B2
Reaction notes
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