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

HRID 1620363노트

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HRID 1620363 반응식
[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]

참가 물질

6

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8e3952d39e5241d6b8e358178305e9dd
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772450B2

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