Dimethylformamide → 6,9-Bis(carboxymethyl)-3-(2,14-dioxo-18,21,24,27,30,33,36-heptaoxa-3,15-diazaheptatriacontanyl)-11,23-dioxo-27,30,33,36,39,42,45-heptaoxa-3,6,9,12,24-pentaazahexatetracontanoic acid

HRID 480538

反応式

HRID 480538 の反応式
O=C1[O:7][C:6](=[O:8])[CH2:5][N:4]([CH2:9][CH2:10][N:11]([CH2:16][CH2:17][N:18]2[CH2:23][C:22](=[O:24])[O:21][C:20](=[O:25])[CH2:19]2)[CH2:12][C:13]([OH:15])=[O:14])[CH2:3]1.[NH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([NH:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][O:60][CH3:61])=[O:38].C[N:63]([CH:65]=[O:66])[CH3:64]>>[C:13]([CH2:12][N:11]([CH2:10][CH2:9][N:4]([CH2:5][C:6]([OH:7])=[O:8])[CH2:3][C:65](=[O:66])[NH:63][CH2:64][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37](=[O:38])[NH:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][O:60][CH3:61])[CH2:16][CH2:17][N:18]([CH2:19][C:20](=[O:25])[NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37](=[O:38])[NH:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][O:60][CH3:61])[CH2:23][C:22]([OH:21])=[O:24])([OH:15])=[O:14]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 100825DTPA dianhydrideHCID 18764642HCID 18764642、化合物

生成物 1

HCID 99420376,9-Bis(carboxymethyl)-3-(2,14-dioxo-18,21,24,27,30,33,36-heptaoxa-3,15-diazaheptatriacontanyl)-11,23-dioxo-27,30,33,36,39,42,45-heptaoxa-3,6,9,12,24-pentaazahexatetracontanoic acid収率 74%

実験手順

N,N-Bis[2-(2,6-dioxo-4-morpholinyl)ethyl]glycine (3.8 g; 10.6 mmol) (commercial product) was added to a suspension of 11-amino-N-(3,6,9,12,15,18,21-heptaoxadocosyl) undecan-amide (11.1 g; 21.1 mmol) in DMF (200 mL). After 15 min the reaction mixture became clear and the conversion was complete. The solvent was evaporated under reduced pressure, the residue was dissolved in CHCl3 and washed with H2O. The organic phase was separated, dried over Na2 SO4 and then evaporated under reduced pressure. The solid was dissolved in H2O and loaded onto an Amberlite® XAD-7 HP resin column (700 mL) and eluted with a CH3CN/H2O gradient. The fraction containing the product was evaporated to give the desired compound (11 g; 7.8 mmol). Yield 74%. HPLC: 85% (area %); K.F. 0.49%. Weight loss (120° C.): 0.45%. The 13C-NMR, MS and IR spectra were consistent with the structure.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in CHCl3
  3. washwashed with H2O
  4. customThe organic phase was separated
  5. customdried over Na2 SO4
  6. customevaporated under reduced pressure
  7. dissolutionThe solid was dissolved in H2O
  8. washeluted with a CH3CN/H2O gradient
  9. additionThe fraction containing the product
  10. customwas evaporated

出典と根拠

ORDレコード
ord-3542142266064229b09d0bd6d40ecd00
出典データセット
uspto-grants-2003_11
特許番号
US06652834B2

関連ノート

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