1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-Butyl (2S)-2-{5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfonylbutyrate

HRID 1251889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251889
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[C:20]([CH:24]=2)[C:21](O)=[O:22])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.[NH2:34][C@@H:35]([CH2:43][CH2:44][S:45]([CH3:48])(=[O:47])=[O:46])[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[C:20]([CH:24]=2)[C:21]([NH:34][C@@H:35]([CH2:43][CH2:44][S:45]([CH3:48])(=[O:47])=[O:46])[C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])=[O:22])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183244905-(1-(4-Fluorophenyl)-2-(imidazol-1-yl)ethoxy)-2-(4-fluorophenethyl)benzoic acidHCID 86585138Tert-butyl (2S)-2-amino-4-methanesulfonylbutanoate

Produkt 1

HCID 57318515tert-Butyl (2S)-2-{5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy]-2-(4-fluorophenethyl)benzoylamino}-4-methylsulfonylbutyrateAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

A mixture of 5-[(1-(4-fluorophenyl)-2-(imidazol-1-yl)ethoxy)]-2-(4-fluorophenethyl)benzoic acid (800 mg, 1.79 mmol), tert-butyl (2S)-2-amino-4-(methylsulfonyl)butanoate (L-methionine sulphone tert-butyl ester) (630 mg, 2.68 mmol), and DMAP (870 mg, 7.1 mmol), was treated with EDC.HCl (510 mg, 2.7 mmol) was stirred at ambient temperature for 16 hours. The reaction mixture was washed with aqueous citirc acid (1M, 2×), brine, dried (MgSO4) and evaporated to dryness. The residue was purified by chromatography on silica (40 gm Dynamax column, gradient elution 2-10% methanol/dichloromethane) to give a gum which, when triturated with diethyl ether/iso-hexane, gave the title compound as a cream solid (889 mg, 74%).

Aufarbeitung

  1. washThe reaction mixture was washed with aqueous citirc acid (1M, 2×), brine
  2. dry with materialdried (MgSO4)
  3. customevaporated to dryness
  4. customThe residue was purified by chromatography on silica (40 gm Dynamax column, gradient elution 2-10% methanol/dichloromethane)
  5. customto give a gum which, when
  6. customtriturated with diethyl ether/iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-6b6d27f5a05445b18b4205d9cfbcbc1a
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342765B1

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