DL-cysteine → 2-(7-(3-Cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 1964085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1964085
[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH:32]([CH3:34])[CH3:33])[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(CS)C(O)=O>C(O)(C(F)(F)F)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH:32]([CH3:34])[CH3:33])[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 67252091tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Produkt 1

HCID 672491622-(7-(3-Cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic AcidAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (452 mg, 0.981 mmol) was added to a solution of 2-amino-3-mercaptopropanoic acid (214 mg, 1.767 mmol) in TFA (5 mL) and was stirred at room temperature for 15 min. The reaction mixture was poured into ice water. The white precipitate was collected by filtration to provide the title compound (342 mg). LCMS m/z=405.5 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.40 (d, J=6.1 Hz, 6H), 2.26-2.36 (m, 1H), 2.66 (dd, J=16.4, 8.5 Hz, 1H), 2.85-2.97 (m, 2H), 3.72-3.80 (m, 1H), 3.98-4.06 (m, 1H), 4.10-4.17 (m, 1H), 4.65 (septet, J=6.1 Hz, 1H), 5.00 (s, 2H), 6.12 (s, 1H), 6.84 (dd, J=8.8, 2.4 Hz, 1H), 6.96 (d, J=8.7 Hz, 1H), 7.06 (d, J=2.4 Hz, 1H), 7.14 (d, J=8.7 Hz, 1H), 7.58 (dd, J=8.8, 2.4 Hz, 1H), 7.64 (d, J=2.1 Hz, 1H).

Aufarbeitung

  1. filtrationThe white precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1efb5ce313cc4f6abbf2e22902cd7047
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415484B2

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