Hydrochloric Acid → HCID 68852261, compound

HRID 1821049Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]([CH3:30])[C:25]([O:27]CC)=[O:26])=[CH:20][C:19]=3[CH3:31])=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Li+].O1CCCC1.Cl>C(OCC)(=O)C.O>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]([CH3:30])[C:25]([OH:27])=[O:26])=[CH:20][C:19]=3[CH3:31])=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

Conditions

Temperature: 55 °C

Procedure

Ethyl (4-(5-(3-cyano-4-(2-propyloxy)phenyl)-thien-2-yl)-3-methylphenyl)propanoate (from STEP E) was combined with 200 mg of lithium hydroxide, 3 mL of tetrahydrofuran and 1 mL of water. The reaction mixture was heated to 55° C. for 6 h, combined with 50 mL of ethyl acetate, 50 mL of 1 M solution of hydrochloric acid. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated. The title compound was isolated by flash chromatography on silica gel using 10% methanol in dichloromethane as the eluant: 1H NMR (CDCl3) 7.81 (d, J=2.0, 1H), 7.74 (dd, J=2.0, 9.0, 1H), 7.38 (d, J=8.0, 1H), 7.22 (d, J=4.0, 1H), 7.16 (d, J=1.0, 1H), 7.11 (dd, J=1.0, 8.0, 1H), 7.03 (d, J=4.0, 1H), 7.00 (d, J=8.0, 1H), 4.70 (sep, J=1.0, 1H), 3.00 (t, J=1.5, 2H), 2.75 (t, J=1.5, 2H), 2.47 (s, 3H), 1.42 (d, J=1.0, 6H); HPLC A 3.78 min; ESI-MS (m/z)=406.

Workup

customThe organic layer was separated
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-91e1b0f76b894f2cbc022d9ecf332285
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605171B2

Reaction notes

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