Trifluoroacetic acid → 2-(4-(2-(4-methoxyphenyl)acetamido)-N-(4-((4-(nonyloxy)benzoyl)oxy)benzyl)benzamido) acetic acid

HRID 923538ノート

反応式

HRID 923538 の反応式
[CH2:1]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C(Cl)(=O)C(Cl)=O.O[C:27]1[CH:62]=[CH:61][C:30]([CH2:31][N:32]([CH2:53][C:54]([O:56]C(C)(C)C)=[O:55])[C:33](=[O:52])[C:34]2[CH:39]=[CH:38][C:37]([NH:40][C:41](=[O:51])[CH2:42][C:43]3[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=3)=[CH:36][CH:35]=2)=[CH:29][CH:28]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CN(C=O)C>[CH3:50][O:49][C:46]1[CH:45]=[CH:44][C:43]([CH2:42][C:41]([NH:40][C:37]2[CH:36]=[CH:35][C:34]([C:33]([N:32]([CH2:53][C:54]([OH:56])=[O:55])[CH2:31][C:30]3[CH:29]=[CH:28][C:27]([O:16][C:15](=[O:17])[C:14]4[CH:13]=[CH:12][C:11]([O:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:19][CH:18]=4)=[CH:62][CH:61]=3)=[O:52])=[CH:39][CH:38]=2)=[O:51])=[CH:48][CH:47]=1

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 65578Oxalyl chlorideHCID 1399924-(Nonyloxy)benzoic acidHCID 71076654tert-butyl 2-(N-(4-hydroxybenzyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetate

生成物 1

HCID 714886472-(4-(2-(4-methoxyphenyl)acetamido)-N-(4-((4-(nonyloxy)benzoyl)oxy)benzyl)benzamido) acetic acid収率 12%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Prepared using General Procedures 2 and 8: To a stirring solution of 4-(nonyloxy)benzoic acid (31 mg, 0.119 mmol) in DCM (0.5 mL) were added DMF (1 drop) and oxalyl chloride (0.011 mL, 0.127 mmol). The reaction mixture was stirred at room temperature for 30 min. To this mixture was added a solution of tert-butyl 2-(N-(4-hydroxybenzyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetate INT-7 (40 mg, 0.079 mmol) and TEA (0.022 mL, 0.159 mmol) in DCM (1 mL). The reaction was stirred at room temperature for 2 h then TFA (1 mL) was added. After stirring for 2 h, the solvent was concentrated and the product was purified by preparative HPLC to afford 6.6 mg (12%) of 2-(4-(2-(4-methoxyphenyl)acetamido)-N-(4-((4-(nonyloxy)benzoyl)oxy)benzyl)benzamido) acetic acid 16. LCMS-ESI (m/z) calculated for C41H46N2O8: 695; found 694 [M−H]−, tR=10.43 min (Method 4). 1H NMR (400 MHz, DMSO) δ 10.30 (s, 1H), 8.05 (d, J=8.8 Hz, 2H), 7.64 (d, J=8.5 Hz, 2H), 7.47-7.27 (m, 4H), 7.23 (d, J=8.0 Hz, 4H), 7.10 (d, J=8.9 Hz, 2H), 6.87 (d, J=8.4 Hz, 2H), 4.62 (d, J=35.9 Hz, 2H), 4.07 (t, J=6.5 Hz, 2H), 3.92 (d, J=40.2 Hz, 2H), 3.71 (s, 3H), 3.56 (s, 2H), 1.85-1.66 (m, 2H), 1.53-1.10 (m, 12H), 0.85 (t, J=6.7 Hz, 3H).

後処理

  1. customPrepared
  2. stirringThe reaction was stirred at room temperature for 2 h
  3. stirringAfter stirring for 2 h
  4. concentrationthe solvent was concentrated
  5. customthe product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-0d64e4074a5b447b8b73a118feb5fee7
出典データセット
uspto-grants-2016_03
特許番号
US09278910B2

反応ノート

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