Triethylamine → 3,6-Bis(carboxymethyl)-9-(10-carboxydecylcarbamoylmethyl)-3,6,9-triazaundecanedioic acid

HRID 1595119ノート

反応式

HRID 1595119 の反応式
[O:1]=[C:2]1[CH2:7][N:6]([CH2:8][CH2:9][N:10]([CH2:15][CH2:16][N:17]([CH2:22][C:23]([O:25]CC)=[O:24])[CH2:18][C:19]([OH:21])=[O:20])[CH2:11][C:12]([OH:14])=[O:13])[CH2:5][C:4](=[O:28])[O:3]1.C(N(CC)CC)C.[NH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48]>CN(C)C=O>[C:19]([CH2:18][N:17]([CH2:16][CH2:15][N:10]([CH2:11][C:12]([OH:14])=[O:13])[CH2:9][CH2:8][N:6]([CH2:7][C:2](=[O:1])[NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48])[CH2:5][C:4]([OH:28])=[O:3])[CH2:22][C:23]([OH:25])=[O:24])([OH:21])=[O:20]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1708311-Aminoundecanoic acidHCID 15745373N3-(2,6-Dioxomorpholinoethyl)-N6-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic Acid

生成物 1

HCID 157453743,6-Bis(carboxymethyl)-9-(10-carboxydecylcarbamoylmethyl)-3,6,9-triazaundecanedioic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

15.33 g (38 mmol) of N3-(2,6-dioxomorpholinoethyl)-N6-(ethoxy-carbonylmethyl)-3,6-diazaoctanedioic acid (Example 13a of EP 0331 616) is suspended in dimethylformamide (DMF) and mixed in an ice bath with 21.07 ml (152 mmol) of triethylamine and 7.65 g (38 mmol) of 11-aminoundecanoic acid. The temperature is allowed to increase to room temperature and the reaction solution is stirred overnight. After completion of the reaction, the possibly still slightly cloudy solution is filtered and the filtrate is concentrated by evaporation in a vacuum. The residue is absorptively precipitated with ether and then recrystallized from water (17.8 g). The ethyl ester is dissolved in 2 N NaOH and is adjusted to pH 7 after 3 hours by adding Amberlite® IR 120 (H+). The ion exchange material is suctioned off, the filtrate is freeze-dried (20.1 g) and then added to H2O/methanol (2:1) on 100 ml of Amberlite® IR 120 (H+) and the acid eluate is concentrated by evaporation and recrystallized from water.

後処理

  1. customAfter completion of the reaction
  2. filtrationthe possibly still slightly cloudy solution is filtered
  3. concentrationthe filtrate is concentrated by evaporation in a vacuum
  4. customThe residue is absorptively precipitated with ether
  5. customrecrystallized from water (17.8 g)
  6. dissolutionThe ethyl ester is dissolved in 2 N NaOH
  7. waitis adjusted to pH 7 after 3 hours
  8. additionby adding Amberlite® IR 120 (H+)
  9. customthe filtrate is freeze-dried (20.1 g)
  10. additionadded to H2O/methanol (2:1) on 100 ml of Amberlite® IR 120 (H+)
  11. concentrationthe acid eluate is concentrated by evaporation
  12. customrecrystallized from water

出典と根拠

ORDレコード
ord-b7b4cc3ca78c44fa9348477d21a7079b
出典データセット
uspto-grants-2001_09
特許番号
US06287538B1

反応ノート

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