1,2-Dichloroethane → (R)-N-(tert-Butoxycarbonyl)-4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamine

HRID 1191045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191045
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:42][C@@H:43]([NH2:48])[C:44]([F:47])([F:46])[F:45]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17](=[O:19])[NH:48][C@H:43]([CH3:42])[C:44]([F:47])([F:46])[F:45])=[CH:14][CH:15]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27559832-(4-((((Tert-butoxy)carbonyl)amino)methyl)phenyl)acetic acidHCID 44593757(R)-2-Amino-1,1,1-trifluoropropane hydrochloride

Produkt 1

HCID 58495584(R)-N-(tert-Butoxycarbonyl)-4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamineAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dissolve [4-(tert-butoxycarbonylamino-methyl)-phenyl]-acetic acid (190 mg, 0.63 mmol) in DCM (12.4 mL) and add triethylamine (354 μL, 2.5 mmol), DMAP (8 mg, 0.063 mmol), EDC (145 mg, 0.756 mmol), HOBt (102 mg, 0.756 mmol) and (R)-1-methyl-2,2,2-trifluoro-ethylamine hydrochloride (71 mg, 0.63 mmol) under nitrogen atmosphere. Stir the reaction overnight at room temperature. Concentrate in vacuo and purify by chromatography on silica gel eluting with hexane/EtOAc (1:1 and 0:1) to obtain the desired intermediate (155 mg, 68%).

Aufarbeitung

  1. customthe reaction overnight at room temperature
  2. concentrationConcentrate in vacuo
  3. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:1 and 0:1)

Quellen und Nachweise

ORD-Eintrag
ord-326b17d185d1400195a1aee386bf9c84
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

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