Hydrochloric Acid → (3R)-4-Amino-3-(3-{[(3,4-dichlorophenyl)sulfonyl]amino}-4-chlorophenyl)butanoic acid

HRID 1799203

Reaktionsgleichung

Reaktionsgleichung von HRID 1799203
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(C(C)C)CC)(C)C.[Cl:24][C:25]1[CH:26]=[C:27]([S:32](Cl)(=[O:34])=[O:33])[CH:28]=[CH:29][C:30]=1[Cl:31].Cl.Cl.NC[C@@H](C1C=CC(Cl)=C(Br)C=1)CC(O)=[O:43]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH2:12][CH2:13][C@@H:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([NH:1][S:32]([C:27]2[CH:28]=[CH:29][C:30]([Cl:31])=[C:25]([Cl:24])[CH:26]=2)(=[O:34])=[O:33])[CH:3]=1)[CH2:10][C:11]([OH:14])=[O:43]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 81531DiisopropylethylamineHCID 66724932(4R)-4-(3-amino-4-chlorophenyl)pyrrolidin-2-oneHCID 66725034(3R)-4-amino-3-(3-bromo-4-chlorophenyl)butanoic acid hydrochloride

Produkt 1

HCID 49793116(3R)-4-Amino-3-(3-{[(3,4-dichlorophenyl)sulfonyl]amino}-4-chlorophenyl)butanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(4R)-4-(3-Amino-4-chlorophenyl)pyrrolidin-2-one (0.105 g, 0.5 mmol) was dissolved in 2 mL of methylene chloride (2 mL). Diisopropylethylamine (0.14 mL, 0.75 mmol) was added followed by 3,4-dichlorobenzenesulfonyl chloride (0.134 g, 0.55 mmol) and a catalytic amount of DMAP (0.05 mmol). The mixture was stirred overnight at room temperature. The mixture was then diluted with methylene chloride (50 mL), washed with water, then brine, and concentrated to give the product, which was treated with HCl as described for the preparation of (3R)-4-amino-3-(3-bromo-4-chlorophenyl)butanoic acid hydrochloride to provide the title compound (21). MS (ESI) m/z 438.89 (M+H)+.

Aufarbeitung

  1. washwashed with water
  2. concentrationbrine, and concentrated
  3. customto give the product, which

Quellen und Nachweise

ORD-Eintrag
ord-b680394f819f43e796659c48df9f4f3a
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344028B2

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