Carbamimidoylazanium Chloride → HCID 178448648、化合物

HRID 733211ノート

反応式

HRID 733211 の反応式
CC(C)([O-])C.[K+].[Cl-].[NH2:8][C:9]([NH2:11])=[NH2+:10].[CH2:12]([N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]1[CH2:26][C:27](OCC)=[O:28])[CH:13]([CH3:15])[CH3:14]>>[CH2:12]([N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]1[CH2:26][C:27]([NH:10][C:9]([NH2:11])=[NH:8])=[O:28])[CH:13]([CH3:15])[CH3:14]

参加物

4

反応物 3

HCID 5460839Carbamimidoylazanium ChlorideHCID 23665647Potassium tert-butoxideHCID 86591359ethyl (2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate

生成物 1

HCID 178448648HCID 178448648、化合物収率 57.3%

反応条件

温度
20 °C

実験手順

(−)-N-[(2-Isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-y)acetyl]guanidine is prepared as described in Example 1, starting with 2.6 g of potassium tert-butoxide, 2.6 g of guanidinium chloride and 1.25 g of ethyl (−)-(2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-y)acetate. The reaction mixture is stirred at a temperature in the region of 20° C. for 40 hours and is then filtered. The filtrate is taken up in 80 cm3 of water and 120 cm3 of ethyl acetate. After separation of the phases by settling, the organic phase is separated out and the aqueous phase is extracted with twice 120 cm3 of ethyl acetate. The organic extracts are combined, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 40° C. The evaporation residue is taken up in 30 cm3 of diethyl ether and the precipitate formed is filtered off and then washed three times with 5 cm3 of diethyl ether. The solid is dried under reduced pressure (10 Pa) at a temperature in the region of 45° C. 0.75 g of (−)-N-[(2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is thus obtained in the form of an off-white solid melting at 264° C. (αD20=−10.2°±0.6 in methanol at 0.5%). Mass spectrum EI: m/e 288 (M+), m/e 245, m/e 201, m/e 132.

後処理

  1. custom(−)-N-[(2-Isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-y)acetyl]guanidine is prepared
  2. filtrationis then filtered
  3. customAfter separation of the phases
  4. customthe organic phase is separated out
  5. extractionthe aqueous phase is extracted with twice 120 cm3 of ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 40° C
  9. customthe precipitate formed
  10. filtrationis filtered off
  11. washwashed three times with 5 cm3 of diethyl ether
  12. customThe solid is dried under reduced pressure (10 Pa) at a temperature in the region of 45° C

出典と根拠

ORDレコード
ord-a8a52673c0c54cf4b2889f38f7ccb0a2
出典データセット
uspto-grants-2009_09
特許番号
US07589117B2

反応ノート

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