Triethylamine → n-(5-Carboxymethyl-pentyl)-2-anthraquinonecarboxamide

HRID 988074

反応式

HRID 988074 の反応式
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1C(O)=O.C1(N=[C:27]=[N:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)CCCCC1.[OH:35]N1C(=O)C2C=CC=CC=2N=N1.C[O:48][C:49](=[O:56])CCCCCN.C(N(CC)CC)C>O1CCCC1>[C:49]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:29][NH:28][C:27]([C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:13](=[O:15])[C:14]=2[CH:1]=1)=[O:35])([OH:48])=[O:56]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 670302-Anthraquinonecarboxylic acidHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 1810164Methyl 6-aminohexanoate

生成物 1

HCID 18006763n-(5-Carboxymethyl-pentyl)-2-anthraquinonecarboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Anthraquinone-2-carboxylic acid (2.52 g, 10 mmol) was suspended in tetrahydrofuran (THF) (100 mL). The mixture was cooled on an ice bath and dicyclohexylcarbodiimide (DCC) (2.26 g, 11 mmol, NovaBiochem) was added, followed by 3-hydroxy-1,2,3-benzotriazine-4-one (Dhbt-OH) (1.63 g, 10 mmol). The ice bath was removed and the mixture stirred overnight at room temperature. The solvent was removed in vacuum and the residue was suspended in DMF (100 ml). 6-aminohexanoic acid methylester (1.99 g, 11 mmol) was added followed by triethylamine (7 mL, 50 mmol). The mixture was stirred overnight at room temperature. DCU was removed by filtration, and the product was precipitated by addition of ice/water (200 mL). The product was collected by filtration and dried in vacuum in an exicator over sicapent. The crude was recrystallized from ethyl acetate yielding the product as yellow solid (3.1 g, 73%). The product was shown to be pure by TLC. R1(ethyl acetate)=0.68. Melting point 144-145° C. Mass spectroscopy (FAB+): 380.1 (MH+). 1H-NMR (DMSO-d6) δ: 9.00 (t, 1H), 8.75 (s, 1H), 8.40 (dd, 1H), 8.30 (m, 3H), 8.05 (m, 2H), 3.70 (s, 3H), 3.40 (q, 2H) 2.40 (t, 2H), 1.70 (qn, 4H), 1.40 (qn, 2H).

後処理

  1. temperatureThe mixture was cooled on an ice bath
  2. customThe ice bath was removed
  3. customThe solvent was removed in vacuum
  4. stirringThe mixture was stirred overnight at room temperature
  5. customDCU was removed by filtration
  6. customthe product was precipitated by addition of ice/water (200 mL)
  7. filtrationThe product was collected by filtration
  8. customdried in vacuum in an exicator over sicapent
  9. customThe crude was recrystallized from ethyl acetate yielding the product as yellow solid (3.1 g, 73%)

出典と根拠

ORDレコード
ord-38ad22d9d89f4905994154793496b9b7
出典データセット
uspto-grants-2003_10
特許番号
US06635434B1

関連ノート

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