Trifluoroacetic acid → (S)-2-(7-chloro-1-oxo-1H-isoquinolin-2-yl)-butyric acid

HRID 655822Notes

Reaction equation

HRID 655822 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C@@H:13]([CH2:21][CH3:22])[C:14]([O:16]C(C)(C)C)=[O:15])[C:9]2=[O:12])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C@@H:13]([CH2:21][CH3:22])[C:14]([OH:16])=[O:15])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57725357tert-Butyl (S)-2-(7-chloro-1-oxoisoquinolin-2(1H)-yl)butanoate

Product 1

HCID 11565197(S)-2-(7-chloro-1-oxo-1H-isoquinolin-2-yl)-butyric acidYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-(7-Chloro-1-oxo-1H-isoquinolin-2-yl)-butyric acid, tert butyl ester (322 mg) in dichloromethane (14 ml) was cooled to 0° C. Trifluoroacetic acid (3.5 ml) was added and the resulting mixture allowed to warm to room temperature and stir for 2 hours. The mixture was then concentrated under reduced pressure and the residue redissolved in dichloromethane. This process was repeated several times in order to remove excess trifluoroacetic acid. The resulting solid was slurried in diethyl ether, filtered and washed with more diethyl ether. The solid was then dried to constant weight under vacuum. This gave the sub-title product as a white solid (236 mg, 89%); m.p. 159.6-160.1° C.; [α]24D-47.00 (c=1.01, CDCl3); it (solid) 1731.4, 1639.3, 1577.8, 1209.1, 1168.1 cm−1; 1H NMR (400 MHz, d6-DMSO) δ 0.82 (3H, t), 2.00-2.25 (2H, m), 5.20 (1H, m), 6.70 (1H, d), 7.49 (1H, d), 7.70-7.81 (2H, m), 8.18 (1H, s); 13C NMR (100 MHz, d6-DMSO) δ 10.8, 22.7, 60.8, 104.9, 126.5, 126.6, 128.8, 131.6, 132.5, 133.1, 135.8, 160.5, 171.7; MS ES (+) 266.27 (M+H).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. dissolutionthe residue redissolved in dichloromethane
  3. customto remove excess trifluoroacetic acid
  4. filtrationfiltered
  5. washwashed with more diethyl ether
  6. customThe solid was then dried to constant weight under vacuum

Sources & evidence

ORD record
ord-bcac73a587d3423298408af9c9b03291
Source dataset
uspto-grants-2011_12
Patent number
US08071618B2

Reaction notes

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