1,2-Dichloroethane → methyl 2-(4-{(S)-{[(4-tert-butylphenyl)-acetyl]amino}[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)-2-methylpropanoate

HRID 877360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877360
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[CH3:16][O:17][C:18](=[O:41])[C:19]([N:22]1[CH:26]=[C:25]([C@H:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[CH:31]C=2)[NH3+:28])[N:24]=[N:23]1)([CH3:21])[CH3:20].C1C=[N:46]C2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([NH:28][C@H:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]([F:39])([F:38])[F:40])=[CH:31][N:46]=2)[C:25]2[N:24]=[N:23][N:22]([C:19]([CH3:20])([CH3:21])[C:18]([O:17][CH3:16])=[O:41])[CH:26]=2)=[O:14])=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 118343Benzeneacetic acid, 4-(1,1-dimethylethyl)-HCID 181649HOAtHCID 86668960(S)-[1-(2-methoxy-1,1-dimethyl-2-oxoethyl)-1H-1,2,3-triazol-4-yl][4-(2,2,2-trifluoroethoxy)phenyl]methanaminium chloride

Produkt 1

HCID 68156240methyl 2-(4-{(S)-{[(4-tert-butylphenyl)-acetyl]amino}[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)-2-methylpropanoateAusbeute 42,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 0.05 g (0.26 mmol) (4-tert-butylphenyl)acetic acid in 0.50 ml CH2Cl2 was added 0.12 g (0.26 mmol) (S)-[1-(2-methoxy-1,1-dimethyl-2-oxoethyl)-1H-1,2,3-triazol-4-yl][4-(2,2,2-trifluoroethoxy)phenyl]methanaminium chloride, 0.05 g (0.34 mmol) HOAT, 0.07 g (0.34 mmol) EDC, and 0.14 ml (0.78 mmol) triethylamine. After 1 h at room temperature, the reaction mixture was diluted with CH2Cl2, and washed twice with water. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. Purification by preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18) afforded 0.06 g (42%) methyl 2-(4-{(S)-{[(4-tert-butylphenyl)acetyl]amino}[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)-2-methylpropanoate. ES-MS [M+1]+=548.3.

Aufarbeitung

  1. washwashed twice with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. additionby preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18)

Quellen und Nachweise

ORD-Eintrag
ord-f3898318f89545faa80dbb31d13d2a67
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987310B2

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