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

HRID 923538노트

반응식

HRID 923538 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0d64e4074a5b447b8b73a118feb5fee7
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278910B2

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