Hydrochloric Acid → HCID 11654374, compound

HRID 1821043Notes

Reaction equation

[Li+].[OH-].[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[S:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:22][C:21]=3[CH3:33])=[N:17][CH:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4].Cl>O.C1COCC1>[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[S:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][C:21]=3[CH3:33])=[N:17][CH:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 2 mg of LiOH in 1 mL water and 1 mL THF was added to ethyl 3-(4-(5-(3-cyano-4-isopropyloxyphenyl)-1,3-thiazol-2-yl)-3-methylphenyl)propanoate (0.003 g, from Step E) and the reaction was heated at 50° C. for 2 h. The reaction was acidified with 0.5 M HCl (25 mL) and the product was extracted with ethyl acetate (25 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with 10% methanol/methylene chloride yielded 1.8 mg of the title compound: 1H NMR (500 MHZ, CDCl3) δ 7.99 (s, 1H), 7.79 (d, J=2.0 Hz, 1H), 7.75 (dd, J=6.9, 2.0 Hz, 1H), 7.72 (d, J=8.0 Hz, 1H), 7.20 (s, 1H), 7.18 (d, J=8.0 Hz, 1H), 7.05 (d, J=8.7 Hz, 1H), 4.70-4.77 (m, 1H), 3.02 (t, J=7.7 Hz, 2H), 2.76 (t, J=7.7 Hz, 2H), 2.64 (s, 3H), 1.47 (d, J=6.0 Hz, 6H).

Workup

extractionthe product was extracted with ethyl acetate (25 mL)
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
washSilica gel chromatography eluting with 10% methanol/methylene chloride

Sources & evidence

ORD record: ord-96a0b0e1c1b64fc09faf2fae39a4d38f
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605171B2

Reaction notes

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