Water → Racemic-(trans)-2-{4-[({5-[4-(trifluoromethyl)phenyl]-2-thienyl}methyl)amino]phenyl}cyclopropanecarboxylic acid trifluoroacetate

HRID 1173010

Reaktionsgleichung

Reaktionsgleichung von HRID 1173010
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[F:14][C:15]([F:30])([F:29])[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[S:26][C:25]([CH:27]=O)=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH2:45]>ClC(Cl)C>[F:14][C:15]([F:30])([F:29])[C:16]([OH:12])=[O:45].[F:30][C:15]([F:14])([F:29])[C:16]1[CH:17]=[CH:18][C:19]([C:22]2[S:26][C:25]([CH2:27][NH:1][C:2]3[CH:3]=[CH:4][C:5]([C@@H:8]4[CH2:10][C@H:9]4[C:11]([OH:13])=[O:12])=[CH:6][CH:7]=3)=[CH:24][CH:23]=2)=[CH:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 46748195-(4-(Trifluoromethyl)phenyl)thiophene-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68668314(1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

Produkt 1

HCID 87568592Racemic-(trans)-2-{4-[({5-[4-(trifluoromethyl)phenyl]-2-thienyl}methyl)amino]phenyl}cyclopropanecarboxylic acid trifluoroacetateAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a mixture of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.058 g, 0.327 mmol) in dichloroethane (2.5 mL) was added 5-[4-(trifluoromethyl)phenyl]-2-thiophenecarbaldehyde (0.071 0.277 mmol). The mixture was stirred for 12 h followed by addition of sodium triacetoxyborohydride (0.090 g, 0.425 mmol). The mixture was stirred for 7 h at RT. Water was added (10 mL), and the layers were separated. The aqueous phase was extracted with EtOAc (3×10 mL). The combined organics were dried with MgSO4 and concentrated. The crude material was purified by preparative HPLC (10% to 100% CH3CN/H2O with 0.05% TFA) to give the title compound as a yellow solid (0.048 g, 15%). 1H NMR (400 MHz, DMSO-d8): δ7.77 (d, J=8.2 Hz, 2H), 7.69 (d, J=8.4 Hz, 2H), 7.51 (d, J=3.7 Hz, 1H), 7.06 (d, J=3.7 Hz, 1H), 6.85 (d, J=8.4 Hz, 2H), 6.55 (d, J=8.6 Hz, 2H), 4.43 (s, 2H), 2.19 (m, 1H), 1.59 (m, 1H), 1.28 (m, 1H), 1.18 (m, 1H). ES-MS m/z 416.03 (MH−).

Aufarbeitung

  1. stirringThe mixture was stirred for 7 h at RT
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organics were dried with MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified by preparative HPLC (10% to 100% CH3CN/H2O with 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-8aa135fd046d40bc8867f987d514c1e7
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834013B2

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