Toluene → HCID 86691513, compound

HRID 588260Notes

Reaction equation

HRID 588260 reaction equation
C([O:5][C:6](=[O:30])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12](=[O:15])[CH:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[CH:18][CH:17]=2)[CH2:10]1)(C)(C)C.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32].C1(C)C=CC=CC=1>C(Cl)Cl>[F:34][C:33]([F:36])([F:35])[C:31]([OH:37])=[O:32].[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[O:22][C:19]1[CH:20]=[CH:21][C:16]([CH:11]2[S:12](=[O:15])[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][C:6]([OH:30])=[O:5])[CH2:10]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 66656124HCID 66656124, compound

Product 1

HCID 86691513HCID 86691513, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{2-[4-(2-Chloro-phenoxy)-phenyl]-1-oxo-thiomorpholin-4-yl}-propionic acid tert-butyl ester (0.19 g; 0.42 mmol) in CH2Cl2 (10 mL) was added TFA (2 mL). The resulting mixture was stirred, at RT, overnight, treated with toluene, and concentrated in vacuo. The residue was dissolved in CH2Cl2 and concentrated in vacuo to afford 3-{2-[4-(2-Chloro-phenoxy)-phenyl]-1-oxo-thiomorpholin-4-yl}-propionic acid trifluoroacetic acid salt as an oil (0.17 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.83 (t, J=8 Hz, 2H), 2.92-3.13 (m, 1H), 3.21-3.34 (m, 2H), 3.34-3.44 (m, 2H), 3.44-3.61 (m, 2H), 3.86 (t, J=12 Hz, 1H), 4.44 (d, J=12 Hz, 1H), 7.04 (m, 2H), 7.23 (d, J=8 Hz, 1H), 7.33 (m, 1H), 7.40 (dd, J=8 and 2 Hz, 1H), 7.47 (m, 2H), 7.69 (dd, J=8 and 2 Hz, 1H), 11.00-13.00 (bs, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3742229c830e4eafad94e08873aaa678
Source dataset
uspto-grants-2016_01
Patent number
US09227960B2

Reaction notes

Loading…