(3S)-3-Amino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic Acid Tert-Butyl Ester → (S,S)-3-[2-(7-trifluoromethyl-1-oxo-1H-isoquinolin-2-yl)-butyrylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic Acid

HRID 1091445Notes

Reaction equation

HRID 1091445 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]([C@@H:14]([CH2:18][CH3:19])[C:15](O)=[O:16])[C:10]2=[O:13])=[CH:5][CH:4]=1.C([O:26][C:27](=[O:45])[CH2:28][C@H:29]([NH2:44])[CH:30]([OH:43])[CH2:31][O:32][C:33]1[C:38]([F:39])=[C:37]([F:40])[CH:36]=[C:35]([F:41])[C:34]=1[F:42])(C)(C)C>>[F:20][C:2]([F:1])([F:21])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]([C@@H:14]([CH2:18][CH3:19])[C:15]([NH:44][C@H:29]([C:30](=[O:43])[CH2:31][O:32][C:33]3[C:38]([F:39])=[C:37]([F:40])[CH:36]=[C:35]([F:41])[C:34]=3[F:42])[CH2:28][C:27]([OH:45])=[O:26])=[O:16])[C:10]2=[O:13])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 44604220(3S)-3-Amino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic Acid Tert-Butyl EsterHCID 66593818(S)-2-(7-trifluoromethyl-1-oxo-1H-isoquinolin-2-yl)-butyric acid

Product 1

HCID 10257542(S,S)-3-[2-(7-trifluoromethyl-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-(7-trifluoromethyl-1-oxo-1H-isoquinolin-2-yl)-butyric acid (prepared as described in methods A-E, see example 2) 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 product was isolated as a white solid (90% last step). IR (solid) 1791.6, 1649.5, 1516.8, 1493.1, 1322.5 cm−1; 1H NMR (400 MHz, d6-DMSO) δ 0.85 (3H, t), 1.90-2.20 (2H, 2×m), 2.50-2.90 (2H, 2×m), 4.70 (1H, m), 5.25 (2H, dd), 5.45 (1H, m), 6.80 (1H, d), 7.65 (1H, m), 7.70 (1H, d), 7.95 (1H, d), 8.05 (1H, d), 8.45 (1H, s), 9.00 (1H, d) ppm; 19F NMR (376 MHz, d6-DMSO) (proton decoupled) δ −56.60, −70.15, −136.38, −152.08.

Workup

  1. customThis compound was prepared
  2. customThe product was isolated as a white solid (90% last step)

Sources & evidence

ORD record
ord-72500f2269d44652a28d5cfb318c8760
Source dataset
uspto-grants-2012_03
Patent number
US08129381B2

Reaction notes

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