Triethylamine → 4-[[(R)-2-(3,4-Dichloro-phenylamino)-propionyl]-(2,2-dimethoxy-ethyl)-amino]-butyric acid tert-butyl ester

HRID 2095575

Reaktionsgleichung

Reaktionsgleichung von HRID 2095575
[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][CH2:9][NH:10][CH2:11][CH:12]([O:15][CH3:16])[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C@H:27]([CH3:31])[C:28](O)=[O:29])[CH:22]=[CH:23][C:24]=1[Cl:25].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.OS([O-])(=O)=O.[K+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][CH2:9][N:10]([C:28](=[O:29])[C@H:27]([NH:26][C:21]1[CH:22]=[CH:23][C:24]([Cl:25])=[C:19]([Cl:18])[CH:20]=1)[CH3:31])[CH2:11][CH:12]([O:13][CH3:14])[O:15][CH3:16])([CH3:3])([CH3:4])[CH3:2]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 182146(R)-2-(3,4-Dichloro-phenylamino)-propionic acid2×HCID 516920Potassium bisulfateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866526894-(2,2-Dimethoxy-ethylamino)-butyric acid tert-butyl ester2×

Produkt 1

HCID 670748224-[[(R)-2-(3,4-Dichloro-phenylamino)-propionyl]-(2,2-dimethoxy-ethyl)-amino]-butyric acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 0.99 g (4.00 mmol) of 4-(2,2-dimethoxy-ethylamino)-butyric acid tert-butyl ester (intermediate 30) in 24 ml of DMF was treated with 1.03 ml (4.40 mmol) of (R)-2-(3,4-dichloro-phenylamino)-propionic acid (62% ee) (intermediate 31), 0.48 ml (4.40 mmol) of triethylamine and at 0° C. with 2.28 g (6.00 mmol) of HATU. Over night, the suspension was naturally warmed to RT, poured on aqueous 10% KHSO4 solution and extracted with Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl, dried (Na2SO4) and evaporated to give after purification with flash chromatography (SiO2, dichloromethane/Et2O 97.5:2.5 to 4:1) 1.37 g (74%) of the titled compound as light yellow viscous oil. MS: 463.17 (MH+, 2Cl).

Aufarbeitung

  1. waitOver night
  2. extractionextracted with Et2O (3×)
  3. washThe organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give
  7. customafter purification with flash chromatography (SiO2, dichloromethane/Et2O 97.5:2.5 to 4:1) 1.37 g (74%) of the titled compound as light yellow viscous oil

Quellen und Nachweise

ORD-Eintrag
ord-8446c34e150e4374843ab86150ef85bb
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445674B2

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