Water → Hexyl 2-[3-(aminocarbonyl)-2,4-difluorophenoxy]acetate
Reaction equation
[NH2:1][C:2]([C:4]1[C:5]([F:16])=[C:6]([CH:12]=[CH:13][C:14]=1[F:15])[O:7][CH2:8][C:9]([OH:11])=[O:10])=[O:3].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[NH2:1][C:2]([C:4]1[C:5]([F:16])=[C:6]([CH:12]=[CH:13][C:14]=1[F:15])[O:7][CH2:8][C:9]([O:11][CH2:6][CH2:5][CH2:4][CH2:14][CH2:13][CH3:12])=[O:10])=[O:3]Participants
5
Conditions
- Temperature
- 70 °C
Procedure
n-Bromohexane (0.077 ml, 0.55 mmol, 1.05 equiv.) was added to a suspension of 2-[3-(aminocarbonyl)-2,4-difluorophenoxy]acetic acid (120 mg, 0.52 mmol, 1 equiv.) and K2CO3 (215 mg, 1.56 mmol, 3 equiv.) in DMF (3 ml) and the mixture was stirred at 70° C. for 1.5 h. After cooling at r.t., the mixture was poured into water (25 ml) and the precipitant solid was filtered and washed with water (2×20 ml). After drying, the crude solid was triturated by stirring in hexane (10 ml), filtered and washed with hexane (3×10 ml), to give the desired compound as a white solid (99 mg, 60%), mp 108° C. HPLC-MS: m/z 316 [M+H]+, Rt=4.09 min.
Workup
- temperatureAfter cooling at r.t.
- filtrationthe precipitant solid was filtered
- washwashed with water (2×20 ml)
- customAfter drying
- customthe crude solid was triturated
- stirringby stirring in hexane (10 ml)
- filtrationfiltered
- washwashed with hexane (3×10 ml)
Sources & evidence
- ORD record
- ord-44163166c90e4a45be05eebeeac351f4
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865736B2
Reaction notes
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