Ammonium Chloride → trans-Cyclohexanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester

HRID 1166446ノート

反応式

HRID 1166446 の反応式
[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]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 11253896Cyclohexanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester, (1s,2r)-

生成物 1

HCID 10777538trans-Cyclohexanecarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, methyl ester収率 64.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  1. customdried flask under nitrogen atmosphere
  2. addition10 mL of freshly distilled methanol was added
  3. dissolutiondissolved
  4. temperatureThe solution was refluxed under nitrogen for 5.5 h
  5. temperaturecooled to rt
  6. customThe methanol was removed under reduced pressure
  7. filtrationthe resulting solid collected by filtration

出典と根拠

ORDレコード
ord-32e4d0cbc47344faa24508f9dfb3aa50
出典データセット
uspto-grants-2003_09
特許番号
US06613876B1

反応ノート

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