Phthalaldehydic acid → (S,S)-3-[2-(1-oxo-1H-isoquinolin-2-yl)-butyrylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid

HRID 1091439Notes

Reaction equation

HRID 1091439 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]1[C@@H:12]([CH2:16][CH3:17])[C:13]([OH:15])=O.C(C1C=CC=CC=1C(O)=O)=O.C([O:33][C:34](=[O:52])[CH2:35][C@H:36]([NH2:51])[CH:37]([OH:50])[CH2:38][O:39][C:40]1[C:45]([F:46])=[C:44]([F:47])[CH:43]=[C:42]([F:48])[C:41]=1[F:49])(C)(C)C>>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]1[C@@H:12]([CH2:16][CH3:17])[C:13]([NH:51][C@H:36]([C:37](=[O:50])[CH2:38][O:39][C:40]1[C:45]([F:46])=[C:44]([F:47])[CH:43]=[C:42]([F:48])[C:41]=1[F:49])[CH2:35][C:34]([OH:52])=[O:33])=[O:15]

Participants

4

Reactant 3

HCID 8406Phthalaldehydic acidHCID 44604220(3S)-3-Amino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic Acid Tert-Butyl EsterHCID 66593632(S)-2-(1-oxo-1H-isoquinolin-2-yl)-butyric acid

Product 1

HCID 10346154(S,S)-3-[2-(1-oxo-1H-isoquinolin-2-yl)-butyrylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid

Procedure

This compound was prepared using (S)-2-(1-oxo-1H-isoquinolin-2-yl)-butyric acid (prepared from 2-formylbenzoic acid using procedures similar to those described in methods A-E) and (3S)-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester (prepared as described in methods N-P) using procedures similar to those described in methods F, G and E. The title compound was isolated by preparative HPLC. IR (solid) 2960.2, 1780.1, 1746.2, 1646.6, 1619.0, 1589.1, 1517.4, 1490.3, 1427.8, 1260.3, 1206.2, 1176.3, 1098.9, 938.4, 788.1, 748.3, 714.2, 692.5, 665.3 and 655.8 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 0.78-0.83 (3H, m), 1.89-1.96 (1H, m), 2.08-2.13 (1H, m), 2.50-2.78 (2H, m), 4.35-5.45 (4H, 3×m), 6.64-6.69 (1H, m), 7.74-7.73 (5H, m), 8.18-8.20 (1H, m), 8.81 & 8.90 (1H, d) ppm; 19F NMR (376 MHz, DMSO) (proton decoupled) δ −141.01, −141.03, −141.07, −141.09, −156.80, −156.82, −156.86, −156.88; MS ES (+) 509.2 (M+H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b1eb5f09eba34abfb132fb1fe18209ed
Source dataset
uspto-grants-2012_03
Patent number
US08129381B2

Reaction notes

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