Lithium Hydroxide → HCID 56602324, compound

HRID 514046Notes

Reaction equation

[C:1]([O:5][CH:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[C:23]#[C:24][CH2:25][N:26]([CH3:28])[CH3:27])[C:13]=1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.C(O)C.O>[C:1]([O:5][CH:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[C:23]#[C:24][CH2:25][N:26]([CH3:27])[CH3:28])[C:13]=1[C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-5-(3-(dimethylamino)prop-1-ynyl)-3-methylnaphthalen-2-yl)acetate (6.5 mg, 0.013 mmol) in tetrahydrofuran:ethanol:water (2:2:1, 4 mL) was added lithium hydroxide (2 mg, 0.066 mmol) and the reaction was heated to 50° C. overnight. The reaction was purified by reverse phase HPLC (Gemini, 40-60% ACN/H2O+0.1% TFA). The product was lyophilized to give a white powder (1.2 mg). 1H-NMR: 400 MHz, (CD3OD) δ: 8.14 (s, 1H), 7.74 (d, J=6.4 Hz, 1H), 7.58 (s, 2H), 7.56 (as, 1H), 7.33 (m, 3H), 5.18 (s, 1H), 4.42 (s, 2H), 3.04 (s, 6H), 2.67 (s, 3H), 0.99 (s, 9H). LCMS-ESI+ (m/z): [M+H]+ calcd for C28H31ClNO3: 464.19; found: 464.51.

Workup

customThe reaction was purified by reverse phase HPLC (Gemini, 40-60% ACN/H2O+0.1% TFA)

Sources & evidence

ORD record: ord-8032f20b84424f478d37b38c90089869
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102614B2

Reaction notes

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