Trifluoroacetic acid → (2R,3R)-3-((2S)-1-(tert-Butoxycarbonyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoic acid

HRID 1772385

Reaktionsgleichung

Reaktionsgleichung von HRID 1772385
[CH3:1][O:2][C@@H:3]([C@@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@@H:4]([CH3:21])[C:5](=[O:20])N[C@H](C1SC=CN=1)CC1C=CC=CC=1.FC(F)(F)C(O)=[O:37]>ClCCl>[C:30]([O:29][C:27]([N:23]1[CH2:24][CH2:25][CH2:26][C@H:22]1[C@H:3]([O:2][CH3:1])[C@@H:4]([CH3:21])[C:5]([OH:20])=[O:37])=[O:28])([CH3:33])([CH3:32])[CH3:31]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 14753401tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidine-1-carboxylate

Produkt 1

HCID 11033491(2R,3R)-3-((2S)-1-(tert-Butoxycarbonyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Synthesis of (2R,3R)-3-methoxy-2-methyl-N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]-3-[(2S)-pyrrolidin-2-yl]propanamide, trifluoroacetic acid salt (#19). According to general procedure B, from #16 (607 mg, 1.28 mmol, 1 eq.), dichloromethane (10 mL, 0.13 M) and trifluoroacetic acid (2 mL) was synthesized #19 (640 mg, quantitative), which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.96-9.07 (br m, 1H), 8.89 (d, J=8.8 Hz, 1H), 7.87-8.00 (br m, 1H), 7.80 (d, J=3.2 Hz, 1H), 7.66 (d, J=3.3 Hz, 1H), 7.28-7.34 (m, 4H), 7.20-7.27 (m, 1H), 5.43 (ddd, J=11.3, 8.6, 4.2 Hz, 1H), 3.42-3.50 (m, 2H), 3.36 (s, 3H), 3.04-3.14 (br m, 1H), 2.99 (dd, J=14.2, 11.5 Hz, 1H), 2.92-3.02 (m, 1H), 2.78-2.88 (br m, 1H), 2.34-2.42 (m, 1H), 1.73-1.84 (br m, 1H), 1.55-1.68 (m, 1H), 1.38-1.53 (m, 2H), 1.15 (d, J=6.9 Hz, 3H).

Aufarbeitung

  1. customwas synthesized #19 (640 mg, quantitative), which
  2. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-84bd4ab4a4c74323810726de857b4f63
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249186B2

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