DL-cysteine → HCID 58329592, Verbindung

HRID 515688

Reaktionsgleichung

Reaktionsgleichung von HRID 515688
[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[C:12]3=[CH:11][C:10]=2[CH:9]=1)#[N:2].NC(C(O)=O)CS>FC(F)(F)C(O)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([OH:23])=[O:22])[C:12]3=[CH:11][C:10]=2[CH:9]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 594DL-cysteineHCID 67249284tert-Butyl 2-(7-(3-Cyano-4-cyclohexylbenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Produkt 1

HCID 58329592HCID 58329592, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To tert-butyl 2-(7-(3-cyano-4-cyclohexylbenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (51.4 mg, 0.106 mmol) was added a solution of DL-cysteine (19.87 mg, 0.159 mmol) in trifluoroacetic acid (1 mL). The mixture was stirred at room temperature for 15 min. The reaction mixture was poured into an ice water to form a solid. The solid was filtered and washed with water to provide the title compound as an off-white solid (41.8 mg). LCMS m/z=429.6 [M+H]+; 1H NMR (400 MHz, DMSO-d6) α ppm 1.19-1.31 (m, 1H), 1.32-1.55 (m, 4H), 1.69-1.75 (m, 1H), 1.75-1.85 (m, 4H), 2.14-2.25 (m, 1H), 2.56 (dd, J=12.00, 8.00 Hz, 1H), 2.67 (dd, J=12.00, 8.00 Hz, 1H), 2.71-2.78 (m, 1H), 2.79-2.90 (m, 1H), 3.57 (t, J=7.39 Hz, 1H), 3.87-3.99 (m, 1H), 4.02-4.16 (m, 1H), 5.08 (s, 2H), 6.00 (s, 1H), 6.76 (dd, J=8.72, 2.40 Hz, 1H), 7.05 (d, J=2.40 Hz, 1H), 7.18 (d, J=8.72 Hz, 1H), 7.51 (d, J=8.21 Hz, 1H), 7.72 (dd, J=8.21, 1.64 Hz, 1H), 7.81 (d, J=1.52 Hz, 1H), 12.26 (bs, 1H).

Aufarbeitung

  1. customto form a solid
  2. filtrationThe solid was filtered
  3. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-6bebec87226648b59459ad9e6ad0cb6e
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108969B2

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