Triethylamine → benzyl 4-(3-cyanophenoxy)-3-(3R)-[4-(pyrrolidine-1-carbonyl)benzoylamino]butyrate

HRID 747784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747784
Cl.[NH2:2][C@@H:3]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=1)[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[N:54]1([C:59]([C:61]2[CH:69]=[CH:68][C:64]([C:65](O)=[O:66])=[CH:63][CH:62]=2)=[O:60])[CH2:58][CH2:57][CH2:56][CH2:55]1>ClCCl>[C:23]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][CH2:15][C@H:3]([NH:2][C:65](=[O:66])[C:64]1[CH:63]=[CH:62][C:61]([C:59]([N:54]2[CH2:58][CH2:57][CH2:56][CH2:55]2)=[O:60])=[CH:69][CH:68]=1)[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])#[N:24]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10932939Benzoic acid, 4-(1-pyrrolidinylcarbonyl)-HCID 86760704benzyl (3R)-3-amino-4-(3-cyanophenoxy)butyrate hydrochloride

Produkt 1

HCID 68832164benzyl 4-(3-cyanophenoxy)-3-(3R)-[4-(pyrrolidine-1-carbonyl)benzoylamino]butyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.8 g (5.2 mmol) of benzyl (3R)-3-amino-4-(3-cyanophenoxy)butyrate hydrochloride (the compound in step 2 in Example 52), 703 mg (5.2 mmol) of 1-hydroxybenzotriazole (hydrate), 997 mg (5.2 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride, 526 mg (5.2 mmol) of triethylamine, and 1.14 g (5.2 mmol) of 4-(1-pyrrolidyl carbonyl)benzoic acid were stirred in dichloromethane overnight. The reaction solution was washed with 1 N hydrochloric acid, 1 N aqueous sodium hydroxide and saturated saline and dried over sulfate magnesium anhydride, and the solvent was distilled off. The resulting residue was purified by silica gel chromatography (ethyl acetate) to obtain the title compound.

Aufarbeitung

  1. washThe reaction solution was washed with 1 N hydrochloric acid, 1 N aqueous sodium hydroxide and saturated saline
  2. dry with materialdried over sulfate magnesium anhydride
  3. distillationthe solvent was distilled off
  4. customThe resulting residue was purified by silica gel chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bf80ac5879e1489fa5675e869d7f03b5
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396844B1

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