Sodium Hydroxide → HCID 9825667, compound

HRID 1416739Notes

Reaction equation

Cl.[CH:2]([O:5][C:6]([C:8]1([C:31]([O:33]C(C)C)=[O:32])[O:12][C:11]2[CH:13]=[CH:14][C:15]([CH2:17][CH:18]([NH:20][CH2:21][CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[OH:23])[CH3:19])=[CH:16][C:10]=2[O:9]1)=[O:7])([CH3:4])[CH3:3].[OH-].[Na+]>CC(O)C>[CH:2]([O:5][C:6]([C:8]1([C:31]([OH:33])=[O:32])[O:12][C:11]2[CH:13]=[CH:14][C:15]([CH2:17][CH:18]([NH:20][CH2:21][CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[OH:23])[CH3:19])=[CH:16][C:10]=2[O:9]1)=[O:7])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution of 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-isopropyl ester hydrochloride salt (3.0 g, 5.53 mmol) and 20 mL of i-PrOH was added was added 1N NaOH (11.1 mL, 11.1 mmol). After stirring at 23° C. for 3 days, the mixture was concentrated to dryness, dissolved in 10% MeOH/CH2Cl2, and filtered through a small pad of silica gel. The filtrate was concentrated to a colorless gum, and triturated with Et2O to give 1.0 g (39%) of 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid isopropyl ester as a white solid; 1H NMR (300 MHz, CDCl3): δ 0.93 (d, J=6.1 Hz, 3H), 1.17 (d, J=6.3 Hz, 6H), 2.30-2.53 (m, 2H), 2.67-2.80 (m, 2H), 2.85-3.00 (m, 1H), 4.65-4.75 (brs, 1H), 4.91 (hept, J=6.3 Hz, 1H), 6.52-6.80 (complexm, 3H), 7.17-7.45 (complexm, 4H); MS (ES) m/z (relative intensity): 464 (M+, 100).

Workup

concentrationthe mixture was concentrated to dryness
dissolutiondissolved in 10% MeOH/CH2Cl2
filtrationfiltered through a small pad of silica gel
concentrationThe filtrate was concentrated to a colorless gum
customtriturated with Et2O

Sources & evidence

ORD record: ord-526069592265471691f04cc801e68533
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914339

Reaction notes

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