Trifluoroacetic acid → (S)-2-Amino-3-(4-(phenylsulfonyl)phenyl)propanamide

HRID 600339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600339
[NH2:1][C:2](=[O:28])[C@@H:3]([NH:20]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:20][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)[C:2]([NH2:1])=[O:28]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 57999655(S)-tert-butyl 1-amino-1-oxo-3-(4-(phenylsulfonyl)phenyl)propan-2-ylcarbamate

Produkt 1

HCID 57999691(S)-2-Amino-3-(4-(phenylsulfonyl)phenyl)propanamideAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-tert-butyl 1-amino-1-oxo-3-(4-(phenylsulfonyl)phenyl)propan-2-ylcarbamate (440 mg) in DCM (10 mL) at 0° C. was added TFA (2.51 mL). The mixture was allowed to warm to RT and stirred for 1 h. The mixture was concentrated in vacuo and partitioned between saturated aqueous sodium bicarbonate and ethyl acetate, dried over sodium sulfate, filtered and concentrated in vacuo to leave the subtitle compound (175 mg) as a white solid.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-775f7b830b52419fa054822d94704055
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902181B2

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