Trifluoroacetic acid → 3-(2-((Isopropoxycarbonyl)methyl)-4-(2-(5-methyl-2-morpholinothiazol-4-yl)ethoxy)phenyl)propanoic acid

HRID 1181059Notes

Reaction equation

HRID 1181059 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[S:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][NH:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])(C)(C)C.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:35]([O:34][C:32]([NH:31][CH2:30][C:10]1[CH:11]=[C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[S:21][C:22]=2[CH3:23])[CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][C:6]([OH:38])=[O:5])=[O:33])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 589792873-{2-(Isopropoxycarbonylamino-methyl)-4-[2-(5-methyl-2-morpholin-4-yl-thiazol-4-yl)-ethoxy]-phenyl}-propionic acid tert-butyl ester

Product 1

HCID 98056393-(2-((Isopropoxycarbonyl)methyl)-4-(2-(5-methyl-2-morpholinothiazol-4-yl)ethoxy)phenyl)propanoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{2-(isopropoxycarbonylamino-methyl)-4-[2-(5-methyl-2-morpholin-4-yl-thiazol-4-yl)-ethoxy]-phenyl}-propionic acid tert-butyl ester (387 mg, 0.706 mmol) in CH2Cl2 (10 mL) was treated with anisole (1 mL) then TFA (3 mL). The solution was stirred at room temperature for 2 h and concentrated. The residue was co-evaporated with CCl4 twice, dried under vacuum, triturated with ether, and filtered to obtain the title compound as a white solid (236 mg, 60%), isolated as the trifluoracetic acid salt: 1H NMR (400 MHz, CDCl3) δ 1.12 (d, 6H, J=6.4 Hz), 2.16 (s, 3H), 2.47 (t, 2H, J=7.6 Hz), 2.79 (t, 2H, J=7.6 Hz), 2.87 (t, 2H, J=6.4 Hz), 3.35 (t, 4H, J=4.9 Hz), 3.70 (t, 4H, J=4.9 Hz), 4.07 (t, 2H, J=6.6 Hz), 4.23 (d, 2H, J=5.4 Hz), 4.82 (heptet, 1H, J=6.1 Hz), 5.07 (bs, 1H), 6.63 (dd, 1H, J=2.7, 8.6 Hz), 6.69 (d, 1H, J=2.9 Hz), 6.98 (d, 1H, J=8.3 Hz). MS (ES) m/e 492.1 [M+1].

Workup

  1. concentrationconcentrated
  2. customdried under vacuum
  3. customtriturated with ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-cfcdd4e5489f4bb6a5bc401312ebed1e
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

Loading…