4-Amino-2-fluorobenzoic acid → 2'-Fluorofolic acid

HRID 629675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629675
[N+]([C:4]1[CH:21]=[C:20]([NH:22][CH2:23][C:24]2[N:35]=[C:34]3[C:27]([N:28]=[C:29]([NH:31][C:32]3=[O:33])[NH2:30])=[N:26][CH:25]=2)[CH:19]=[CH:18][C:5]=1[C:6](=[O:17])[NH:7][C@H:8]([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])([O-])=O.NC1C=CC(C(O)=O)=C([F:46])C=1>>[F:46][C:4]1[CH:21]=[C:20]([NH:22][CH2:23][C:24]2[N:35]=[C:34]3[C:27]([N:28]=[C:29]([NH:31][C:32]3=[O:33])[NH2:30])=[N:26][CH:25]=2)[CH:19]=[CH:18][C:5]=1[C:6](=[O:17])[NH:7][C@H:8]([C:14]([OH:16])=[O:15])[CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Komponenten

3

Edukt 2

HCID 3026804-Amino-2-fluorobenzoic acidHCID 1363537692'-Nitrofolic acid

Produkt 1

HCID 1363604892'-Fluorofolic acid

Versuchsvorschrift

The synthesis was done in analogy to the synthesis of 2′-nitrofolic acid following examples 1 to 4. In example 1 4-amino-2-fluoro-benzoic acid was used instead of 4-amino-2-nitrobenzoic acid. (HPLC purity: 97.5% area, m/z=460 [M+1]+, 1H-NMR (200 MHz, DMSO-d6) [ppm]: 8.65 (s, C(7)-H, 1H); 7.75 (t, N(8′)-H, 1H, exchangeable with D2O); 7.51 (t, C(3′H), 1H); 7.20 (t, N(10)-H, 1H, exchangeable with D2O); 7.03 (bs, NH2, 2H, exchangeable with D2O); 6.50 (m, C(5′)-H, (C(6′)-H, 2H); 4.48 (d, C(6)H2, 2H); 4.31 (m, C(α)-H, 1H); 2.28 (m, C(β)-H2, 2H); 1.96 (m, C(γ)-H2, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-e1d3259e3c7e4e51bdd39bf9f11aa86a
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315506B2

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