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

HRID 923542
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 923542
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.O[C:23]1[CH:58]=[CH:57][C:26]([CH2:27][N:28]([CH2:49][C:50]([O:52]C(C)(C)C)=[O:51])[C:29](=[O:48])[C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:47])[CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)=[CH:32][CH:31]=2)=[CH:25][CH:24]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CN(C=O)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][C:23]3[CH:58]=[CH:57][C:26]([CH2:27][N:28]([CH2:49][C:50]([OH:52])=[O:51])[C:29](=[O:48])[C:30]4[CH:31]=[CH:32][C:33]([NH:36][C:37](=[O:47])[CH2:38][C:39]5[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=5)=[CH:34][CH:35]=4)=[CH:25][CH:24]=3)=[O:12])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
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Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 65578Oxalyl chlorideHCID 883374-Cyclohexylbenzoic acidHCID 71076654tert-butyl 2-(N-(4-hydroxybenzyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetate

Produkt 1

HCID 714887732-(N-(4-((4-cyclohexylbenzoyl)oxy)benzyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido) acetic acid
Ausbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Prepared using General Procedures 2 and 8: To a stirring solution of 4-cyclohexylbenzoic acid (24 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 2 h. 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 18 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 provide to afford 22.2 mg (44%) of 2-(N-(4-((4-cyclohexylbenzoyl)oxy)benzyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido) acetic acid 39. LCMS-ESI (m/z) calculated for C38H38N2O7: 634; found 633 [M−H]−, tR=8.92 min (Method 4). 1H NMR (400 MHz, DMSO) δ 10.30 (s, 1H), 8.04 (d, J=7.7 Hz, 2H), 7.64 (d, J=8.2 Hz, 2H), 7.45 (t, J=7.0 Hz, 3H), 7.39-7.26 (m, 3H), 7.24 (d, J=8.4 Hz, 4H), 6.88 (d, J=8.1 Hz, 2H), 4.62 (d, J=36.7 Hz, 2H), 3.94 (d, J=31.7 Hz, 2H), 3.72 (s, 2H), 3.57 (s, 3H), 2.63 (t, J=10.7 Hz, 1H), 1.76 (dd, J=36.3, 11.5 Hz, 5H), 1.53-1.16 (m, 5H).

Aufarbeitung

  1. customPrepared
  2. stirringThe reaction was stirred at room temperature for 18 h
  3. stirringAfter stirring for 2 h
  4. concentrationthe solvent was concentrated
  5. customthe product was purified by preparative HPLC
  6. customto provide

Quellen und Nachweise

ORD-Eintrag
ord-5ce2e720124c44308265d12fc4276daf
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09278910B2

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