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

HRID 1432364Notes

Reaction equation

HRID 1432364 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:29]([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])([CH3:32])([CH3:31])[CH3:30]>>[C:29]([O:33][C:34](=[O:52])[CH2:35][C@H:36]([NH:51][C:13](=[O:15])[C@@H:12]([N:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]1=[O:1])[CH2:16][CH3:17])[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])([CH3:32])([CH3:30])[CH3:31]

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 86594402(S,S)-3-[2-(1-oxo-1H-isoquinolin-2-yl)-butyrylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert butyl ester

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 H-J) using procedures similar to those described in methods F-G. This compound was isolated as a white solid This compound was prepared using methods similar to A-G and was isolated as a white solid 1H NMR (400 MHz CDCl3) δ 0.98 (3H, t), 1.30 (9H, s), 1.98-2.02 (1H, m), 2.26-2.32 (1H, m), 2.68 (1H, dd), 2.90 (1H, dd), 4.83-4.88 (1H, m), 5.06 (1H, d), 5.15 (1H, d), 5.50 (1H, t), 6.60 (1H, d), 6.75-6.82 (1H, m), 7.23 (1H, d), 7.33 (1H, d), 7.49-7.55 (1H, m), 7.68 (1H, t), 8.41 (1H, d); 19F NMR (376 MHz, CDCl3) (proton decoupled) δ −139.94, −139.97, −140.0, −140.02. −157/06, −157.09, −157.12, −157.14; ES(+) 565.3, ES(−) 563.3.

Workup

  1. customThis compound was prepared
  2. customThis compound was isolated as a white solid This compound
  3. customwas prepared

Sources & evidence

ORD record
ord-a892b7c3dc3d4ed6bfb1ab81fa24ae86
Source dataset
uspto-grants-2009_11
Patent number
US07612091B2

Reaction notes

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