Isopropylethanediol → Ether hydrochloride

HRID 1416738Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:29])[CH2:9][NH:10][CH:11]([CH3:28])[CH2:12][C:13]2[CH:27]=[CH:26][C:16]3[O:17][C:18]([C:23]([OH:25])=[O:24])([C:20]([OH:22])=[O:21])[O:19][C:15]=3[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[CH:30]([O:33][CH2:34][CH2:35]O)([CH3:32])[CH3:31]>>[CH:16]([O:17][CH2:18][CH2:20][O:24][C:23]([C:18]1([C:20]([O:22][CH2:35][CH2:34][O:33][CH:30]([CH3:31])[CH3:32])=[O:21])[O:17][C:16]2[CH:26]=[CH:27][C:13]([CH2:12][CH:11]([NH:10][CH2:9][CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[OH:29])[CH3:28])=[CH:14][C:15]=2[O:19]1)=[O:25])([CH3:26])[CH3:15].[O:17]([CH2:18][CH3:20])[CH2:16][CH3:15].[ClH:1]

Participants

Reactant 2

HCID 7996Isopropylethanediol

HCID 42813555-{2-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid

Product 2

HCID 10953452Ether hydrochloride

HCID 53860117HCID 53860117, compound

Procedure

The title compound was prepared from 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid and 2-isopropoxyethanol as a brown solid according to the procedure of Example 1, leaving out the final HCl(g) /Et2O hydrochloride salt forming step: 1H NMR (300 MHz, CDCl3): δ 1.11 (d, J=6.1 Hz, 12H), 1.30 (d, J=6.2 Hz, 3H), 2.79 (t, J=8.7 Hz, 1H), 3.06-3.28 (m, 2H), 3.40-3.60 (m, 2H), 3.62-3.70 (complexm, 4H), 3.90-4.12 (brm, 2H), 4.35-4.45 (complexm, 4H), 5.43 (d, J=8.7 Hz, 1H), 6.61-6.90 (m, 3H), 7.11-7.32 (m, 3H), 7.44 (m, 1H), 8.70 (brs, 1H), 9.92 (brs, 1H); MS (ES) m/z (relative intensity): 758 (M+, 30), 546 (100).

Sources & evidence

ORD record: ord-20ffe3cfa1e24fa19ef9066861956216
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914339

Reaction notes

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