Ammonium Chloride → trans-Cyclohexanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester
Reaction equation
[Na].[C:2]([O:6][C:7]([NH:9][C@H:10]1[C@@H:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].C[O-].[Na+].[Cl-].[NH4+]>CO>[C:2]([O:6][C:7]([NH:9][C@H:10]1[C@H:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:8])([CH3:5])([CH3:4])[CH3:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sodium metal (0.14 g, 6.1 mmol) was placed into a flame dried flask under nitrogen atmosphere and cooled to 0° C. 10 mL of freshly distilled methanol was added and the mixture stirred until all the sodium dissolved. An amount of 25 (2.00 g, 7.7 mmol) was dissolved in 10 mL of freshly distilled methanol and transferred to NaOMe solution via cannula. The solution was refluxed under nitrogen for 5.5 h, cooled to rt and acidified with 0.5 M aqueous 0.5 M ammonium chloride (18 mL, 9 mmol). The methanol was removed under reduced pressure, and the resulting solid collected by filtration to yield 1.27 g of desired product.
Workup
- customdried flask under nitrogen atmosphere
- addition10 mL of freshly distilled methanol was added
- dissolutiondissolved
- temperatureThe solution was refluxed under nitrogen for 5.5 h
- temperaturecooled to rt
- customThe methanol was removed under reduced pressure
- filtrationthe resulting solid collected by filtration
Sources & evidence
- ORD record
- ord-2451f1935992406881ebebd4c0b9d907
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06683154B1
Reaction notes
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