Water → HCID 178457334, compound

HRID 2404184Notes

Reaction equation

C[O:2][C:3](=[O:31])[CH2:4][CH2:5][NH:6][C:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH:21]3[CH2:26][CH2:25][CH:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:22]3)[CH:16]=2)[N:11]=1)([CH3:9])[CH3:8].[OH-].[Li+].O1CCCC1.O>>[C:27]([C@H:24]1[CH2:23][CH2:22][C@H:21]([O:20][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[N:11]=[C:10]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:31])=[O:2])([CH3:9])[CH3:8])[CH:19]=[CH:18]3)[CH2:26][CH2:25]1)([CH3:28])([CH3:29])[CH3:30]

Participants

Reactant 4

HCID 962Water

HCID 3939Lithium Hydroxide

HCID 8028Tetrahydrofuran

HCID 70496005HCID 70496005, compound

Product 1

HCID 178457334HCID 178457334, compound

Procedure

A solution of 3-{1-[6-(4-tert-Butyl-cyclohexyloxy)-quinolin-2-yl]-1-methyl-ethylamino}-propionic acid methyl ester (36.0 mg, 0.0844 mmol) and Lithium hydroxide (20.2 mg, 0.844 mmol) in Tetrahydrofuran (1 mL, 20 mmol) and Water (0.3 mL, 20 mmol) was stirred at r.t. overnight. LCMS showed a single desired product peak RT 1.57 min M+1 at m/z 413.30, 100%. The solvent was concentrated and neutralized with citric acid and concentrated and Purified on HPLC to give product (20 mg, 57%). 1H NMR (400 MHz, CHLOROFORM-d) d=8.30 (d, J=8.7 Hz, 1H), 7.97 (d, J=9.2 Hz, 1H), 7.59 (d, J=8.7 Hz, 1H), 7.39 (dd, J=2.7, 9.2 Hz, 1H), 7.30 (d, J=2.5 Hz, 1H), 4.43-4.28 (m, 1H), 3.23 (t, J=6.6 Hz, 2H), 2.84 (t, J=6.6 Hz, 2H), 2.26 (d, J=10.4 Hz, 2H), 1.90 (d, J=13.6 Hz, 2H), 1.79 (s, 6H), 1.49-1.32 (m, 2H), 1.32-1.17 (m, 2H), 1.17-1.00 (m, 1H), 0.90 (s, 9H).

Sources & evidence

ORD record: ord-1d5a6228f7524309b9c07e29b1d97f40
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802659B2

Reaction notes

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