4-Iodophenol → 3-(4-(Carboxymethoxy)-2,2''-diisobutyl-3-naphthalen-1-ylmethyl-[1,1':4',1'']-terphenyl-4''-yl)propionic acid

HRID 25848

반응식

HRID 25848 반응식
[Cl-].[Na+].O.O.Br[C:6]1[CH:7]=[CH:8][C:9]([OH:20])=[C:10]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)[CH:11]=1.C(C1C=C(C2C=CC(CCC#N)=CC=2CC(C)C)C=CC=1C1C=CC(OCC#N)=C(CC2C=CC=CC=2)C=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(C1C=C([C:86]2[CH:91]=[CH:90][C:89](CCC#N)=[CH:88][C:87]=2CC(C)C)C=CC=1OS(C(F)(F)F)(=O)=O)C1C=CC=CC=1.COC1C=CC=[CH:107][C:103]=1[C:104]([OH:106])=[O:105].C(C1C=C(C2C=CC(CCC#N)=CC=2[CH2:136][CH:137]([CH3:139])[CH3:138])C=CC=1OC)C1C=CC=CC=1.C(COC1C=CC(C2C=CC(C3C=CC(CCC#N)=CC=3CC(C)C)=CC=2CC2C3C(=CC=CC=3)C=CC=2)=CC=1[CH2:181][CH:182]([CH3:184])[CH3:183])#N.C(C1C=C(C2C=CC(CCC(O)=O)=CC=2CC(C)C)C=CC=1C1C=CC(O[CH2:205][C:206]([OH:208])=[O:207])=C(CC(C)C)C=1)C1C=CC=CC=1.I[C:229]1[CH:234]=CC(O)=[CH:231][CH:230]=1>CC(O)=O>[C:206]([CH2:205][O:20][C:9]1[CH:8]=[CH:7][C:6]([C:86]2[CH:87]=[CH:88][C:89]([C:27]3[CH:26]=[CH:25][C:24]([CH2:107][CH2:103][C:104]([OH:106])=[O:105])=[CH:23][C:22]=3[CH2:184][CH:182]([CH3:181])[CH3:183])=[CH:90][CH:91]=2)=[C:11]([CH2:139][CH:137]([CH3:136])[CH3:138])[C:10]=1[CH2:12][C:14]1[C:19]2[C:18](=[CH:234][CH:229]=[CH:230][CH:231]=2)[CH:17]=[CH:16][CH:15]=1)([OH:208])=[O:207]

참가 물질

11

반응물 9

HCID 108944-IodophenolHCID 113702-Methoxybenzoic acidHCID 2290095-Bromo-2-hydroxybenzophenoneHCID 10120948Terphenyl scaffold, 16HCID 121347103-(3'-Benzyl-2-isobutyl-4'-methoxy-1,1'-biphenyl-4-yl)propanenitrile2회HCID 12134712Trifluoro-methanesulfonic acid 3-benzyl-4'-(2-Cyano-ethyl)-2'-isobutyl-biphenyl-4-yl esterHCID 121347153-(3',3''-Dibenzyl-4''-(cyanomethoxy)-2-isobutyl-1,1':4',1''-terphenyl-4-yl)propanenitrileHCID 225652383-(4-Cyanomethoxy-3,2''-diisobutyl-2'-naphthalen-1-ylmethyl-[1,1':4',1'']-terphenyl-4''-yl)propionitrileHCID 23713072Sodium chloride dihydrate

생성물 1

HCID 225652143-(4-(Carboxymethoxy)-2,2''-diisobutyl-3-naphthalen-1-ylmethyl-[1,1':4',1'']-terphenyl-4''-yl)propionic acid

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of 36.3 mg (55.26 μmol) 3-(2′,2″-Diisobutyl-4-methoxycarbonylmethoxy-3-naphthalen-1-ylmethyl-[1,1′:4′,1″]-terphenyl-4″-yl)propionic acid methyl ester (79) in 8 ml 1.4-dioxane 2.0 ml (16.60 mmol, 301 eq.) 25% aq. NaOH-solution and 2.0 ml (3.08 mmol, 56 eq.) 40% aq. solution of Bu4NOH were added. The resulting mixture was refluxed for 24 h and then cooled to 0° C. Acidification to pH 1 by adding 1 N aq. HCl-solution led to a white precipitate which was obtained by filtration. A filtration over silica gel with EtOAc/HOAc (95+5)) as an eluent and a following lyophilization of the obtained oily product from a solution in CH3CN and aq. NH3-solution yielded 36.6 mg (55.2 μmol, 100%) of the bisammonia-salt of 3-(4-(Carboxymethoxy)-2,2″-diisobutyl-3-naphthalen-1-ylmethyl-[1,1′:4′,1″]-terphenyl-4″-yl)propionic acid (80) as a white solid. Rf (hexanes/EtOAc (1+1), sample dissolved in HOAc)=0.49. 1H-NMR (500 MHz, d4-MeOH): δ=0.43 (d, 6H, J=6.62 Hz, 2*CH3), 0.65 (d, 6H, J=6.62 Hz, 2*CH3), 1.35 (m, 1H, CH), 1.58 (m, 1H, CH), 2.14 (d, 2H, J=7.41 Hz, CH2), 2.44 (d, 2H, J=7.25 Hz, CH2), 2.56 (t, 2H, J=7.41 Hz, CH2CH2CO2NH4), 2.90 (t, 2H, J=7.57 Hz, CH2CH2NH4), 4.58 (s, 2H, CH2Naphthyl), 4.59 (s, 2H, OCH2CO2NH4), 6.62 (d, 1H, J=2.05 Hz), 6.89-7.08 (m, 8H), 7.38-7.45 (m, 4H), 7.73 (m, 1H), 7.83 (m, 1H), 8.08 (m, 1H). 13C-NMR (125 MHz, d4-MeOH): δ=22.97, 23.13, 30.75, 31.02, 32.69, 33.91, 38.49, 43.45, 43.73, 68.54, 112.71, 126.33, 126.85, 126.92, 126.99, 127.26, 128.00, 128.35, 129.01, 129.22, 129.90, 130.84, 131.09, 131.41, 131.49, 132.31, 132.42, 134.19, 135.91, 135.95, 138.60, 140.16, 140.53, 141.56, 141.86, 142.22, 142.28, 157.00, 177.34, 178.03. MS (FAB−): m/z=629 (18), 628 (29), 627 (54), 570 (42), 569 (100), 568 (16), 567 (24), 527 (24), 526 (30), 525 (70), 524 (30), 523 (58), 481 (30), 347 (14), 153 (96). HR-MS (FAB−): not possible.

출처 및 근거

ORD 기록
ord-2ef9bba2357243bcbd2780dc1a88b8b0
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858600B2

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