Water → HCID 11395919, Verbindung

HRID 1173008

Reaktionsgleichung

Reaktionsgleichung von HRID 1173008
[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]1[CH:16]=[C:17]([O:22][C:23]2[S:24][C:25]([CH:29]=O)=[C:26]([CH3:28])[N:27]=2)[CH:18]=[CH:19][C:20]=1[F:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClC(Cl)C>[F:14][C:15]1[CH:16]=[C:17]([O:22][C:23]2[S:24][C:25]([CH2:29][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)=[C:26]([CH3:28])[N:27]=2)[CH:18]=[CH:19][C:20]=1[F:21]

Komponenten

6

Edukt 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 68668314(1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acidHCID 86053287HCID 86053287, Verbindung

Produkt 1

HCID 11395919HCID 11395919, VerbindungAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a mixture of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.054 g, 0.305 mmol) in dichloroethane (2 mL) was added 2-[(3,4-difluorophenyl)oxy]-4-methyl-1,3-thiazole-5-carbaldehyde (0.072 g, 0.282 mmol). The mixture was stirred for 12 h followed by addition of sodium triacetoxyborohydride (0.092 g, 0.434 mmol). The mixture was stirred for 5 h at RT. Water was added (10 mL), and the layers were separated. The aqueous phase was extracted with CH2Cl2 (2×10 mL). The combined organics were dried with MgSO4 and concentrated. The crude material was purified by chromatography (EtOAc/hexanes) to give the title compound as a yellow solid (0.077 g, 51%). 1H NMR (400 MHz, DMSO-d6): δ 7.59-7.47 (m, 2H), 7.18 (m, 1H), 6.87 (d, J=8.4 Hz, 2H), 6.51 (d, J=8.4 Hz, 2H), 4.23 (s, 2H), 2.47 (m, 1H), 2.17 (s, 3H), 1.59 (m, 1H), 1.29 (m, 1H), 1.18 (m, 1H). ES-MS m/z 416.98 (MH+).

Aufarbeitung

  1. stirringThe mixture was stirred for 5 h at RT
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with CH2Cl2 (2×10 mL)
  4. dry with materialThe combined organics were dried with MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2c020f6067f145b6af6f37c598f23321
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834013B2

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