Hydrochloric Acid → 6-[3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic Acid

HRID 2117212Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 6-[3-(1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic acid methyl ester (110 mg, 0.27 mmol) in (1:1) THF/CH3OH (1 mL) is added 250 μL water and 10N NaOH soln (270 μL). The mixture is stirred for 16 hrs, cooled to 5° C., adjusted to pH 4 with 2N HCl soln. and diluted with EtOAc. The organic layer is washed with brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 50% ethyl acetate/5% methanol/hexanes) to give 67 mg of title compound. 1H NMR (300 MHz, CDCl3) δ 7.29 (m, 3H), 7.14 (d, 1H), 7.09 (d, 1H), 6.63 (dd, 1H), 6.52 (d, 1H), 5.04 (s, 2H), 3.18 (s, 3H), 2.64 (t, 2H), 2.36 (t, 2H), 1.66 (m, 4H), 1.40 (m, 2H), 1.34 (s, 6H). MS (ESI) 396 (M+H)+.

Workup

washThe organic layer is washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue is purified by flash chromatography (eluting with 50% ethyl acetate/5% methanol/hexanes)

Sources & evidence

ORD record: ord-2234d7a02dcc4cf592fe9bc302dcde0f
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE040558E1

Reaction notes

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