Hydrochloric Acid → HCID 44300367, compound

HRID 1416778Notes

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.[O:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[CH2:36]O.[K+].[Br-].Cl>>[O:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[CH2:36][O:24][C:23]([C:18]1([C:20]([O:22][CH2:36][CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35][O:30]2)=[O:21])[O:17][C:16]2[CH:26]=[CH:27][C:13]([CH2:12][C@H:11]([NH:10][CH2:9][C@@H: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]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 7524Tetrahydropyran-2-methanol

HCID 253877Potassium Bromide

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

Product 1

HCID 44300367HCID 44300367, 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 tetrahydropyran-2-ylmethanol according to the procedure of Example 1 as an off-white solid; 1H NMR (DMSO-d6,400 MHz) δ 1.10 (d, J=6.37 Hz, 3H, CH3), 1.1-1.2 (m, 2H, CH2), 1.3-1.6 (m, 8H, CH2), 1.7-1.8 (m, 2H, CH2), 2.6 (m, 1H, CH), 3-3.5 (m, 9H, CH, CH2), 3.8 (m, 2H, CH), 4.19-4.2 (s, s, 4H, OCH2, OCH2), 5.04 (m, 1H, CH), 6.35 (d, J=4.17 Hz, 1H, OH), 6.85 (d, J=8.13 Hz, 1H, Ar--H), 7.07 (m, 2H, Ar--H), 7.36-7.42 (m, 3H, Ar--H), 7.48 (s, 1H, Ar--H), 8.76 (brs, 1H, NH), 9.18 (brs, 1H, NH); IR (KBr, cm-1) 3400 (OH), 2900 (NH), 1760 (CO); MS m/e 618 (M+H)+ ; Analysis for: C32H40ClNO9 ×HCl: Calc'd: C, 58.72; H, 6.31; N, 2.14; Found: C, 57.97; H, 6.46; N, 2.08.

Sources & evidence

ORD record: ord-3e42fe380b7346e4bff0d4161e70b145
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914339

Reaction notes

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