Ammonium Chloride → (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-carbamoyl-2,6-dimethylphenyl)propanoate

HRID 1270821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270821
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22]([O:24][CH3:25])=[O:23])[CH2:10][C:11]1[C:19]([CH3:20])=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][C:12]=1[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C[N:29]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>CN(C=O)C>[CH3:25][O:24][C:22](=[O:23])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][C:11]1[C:19]([CH3:20])=[CH:18][C:14]([C:15](=[O:16])[NH2:29])=[CH:13][C:12]=1[CH3:21]

Komponenten

7

Edukt 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58631279(S)-4-(2-tert-Butoxycarbonylamino-2-methoxycarbonylethyl)-3,5-dimethylbenzoic acid

Produkt 1

HCID 58631271(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-carbamoyl-2,6-dimethylphenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into a stirrng solution of the benzoic acid from Step B (3.00 g, 8.54 mmol), PyBOP (6.68 g, 12.8 mmol) and HOBt (1.74 g, 12.8 mmol) in DMF (36 mL) was added DIPEA (5.96 mL, 34.2 mmol) and NH4Cl (0.92 g, 17.1 mmol). The resulting mixture was stirred at rt for 40 min before being partitioned between aqueous NH4Cl solution and EtOAc. The separated organic phase was washed with 2 N citric acid aqueous solution, saturated aqueous NaHCO3 solution and brine, and dried over Na2SO4 overnight. After concentration, the residue was purified by flash column chromatography (eluent: EtOAc) to give the title amide. 3.00 g, 100%; 1H NMR (300 MHz, CDCl3): δ 1.36 (9H, s), 2.39 (6H, s), 3.11 (2H, J=7.2 Hz), 3.65 (3H, s), 4.53–4.56 (1H, m), 5.12 (1H, d, J=8.7 Hz), 5.65 (1H, br s), 6.09 (1H, br s), 7.46 (2H, s); MS(ES+) (relative intensity): 250.9 (100) (M-Boc)+.

Aufarbeitung

  1. custombefore being partitioned between aqueous NH4Cl solution and EtOAc
  2. washThe separated organic phase was washed with 2 N citric acid aqueous solution, saturated aqueous NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4 overnight
  4. concentrationAfter concentration
  5. customthe residue was purified by flash column chromatography (eluent: EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-a4043d9846064e1697223b317bde450e
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202381B2

Notizen zur Reaktion

Wird geladen…