Trifluoroacetic acid → (S)-1-((S)-1-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl)pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid

HRID 594191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594191
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[C:27]([O:29]C(C)(C)C)=[O:28])=[O:21])=[O:14].FC(F)(F)C(O)=O>ClCCl>[O:7]=[C:4]1[CH:5]=[CH:6][C:2](=[O:1])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[C:27]([OH:29])=[O:28])=[O:21])=[O:14]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67453011(S)-tert-butyl 1-((S)-1-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl)pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylate

Produkt 1

HCID 67452427(S)-1-((S)-1-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl)pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of the tert-butyl ester 77 in dichloromethane (4 mL) was added trifluoroacetic acid (4 mL). After 40 min the reaction was determined to be complete by HPLC analysis. The mixture was concentrated under reduced pressure and the resulting residue was dissolved in dichloromethane and concentrated a second time to give 37 mg (100%) of 78 as a white solid: 1H-NMR (400 MHz, CDCl3) δ 6.68 (s, 2H), 4.62 (m, 2H), 3.81 (m, 1H), 3.70 (m, 1H), 3.57 (m, 2H), 3.45 (m, 2H), 2.40-1.91 (m, 10H), 1.70-1.45 (m, 4H), 1.33 (m, 2H); MS (ES+) m/z 406.2 [M+H]+.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in dichloromethane
  3. concentrationconcentrated a second time

Quellen und Nachweise

ORD-Eintrag
ord-09314b013fc14cb8a6eb2d5804a2dbaa
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242013B2

Notizen zur Reaktion

Wird geladen…