Hydrochloric Acid → HCID 131718522, compound

HRID 1110085Notes

Reaction equation

HRID 1110085 reaction equation
C[O:2][C:3]([C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:19][CH2:20][CH2:21][CH2:22][O:23][C:24]4[CH:29]=[C:28]([OH:30])[C:27]([C:31](=[O:33])[CH3:32])=[CH:26][C:25]=4[CH2:34][CH3:35])[CH:13]=3)[C:8](=[O:36])[C:7]=2[CH:6]=1)=[O:4].[OH-:37].[Na+:38].Cl>CO.O1CCCC1>[OH2:2].[Na+:38].[Na+:38].[C:31]([C:27]1[C:28]([OH:30])=[CH:29][C:24]([O:23][CH2:22][CH2:21][CH2:20][O:19][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:36])[C:7]2[CH:6]=[C:5]([C:3]([O-:4])=[O:2])[CH:18]=[CH:17][C:16]=2[O:15]3)=[C:25]([CH2:34][CH3:35])[CH:26]=1)(=[O:33])[CH3:32].[OH2:37].[OH2:2].[C:31]([C:27]1[C:28]([OH:30])=[CH:29][C:24]([O:23][CH2:22][CH2:21][CH2:20][O:19][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:36])[C:7]2[CH:6]=[C:5]([C:3]([O-:4])=[O:2])[CH:18]=[CH:17][C:16]=2[O:15]3)=[C:25]([CH2:34][CH3:35])[CH:26]=1)(=[O:33])[CH3:32].[C:31]([C:27]1[C:28]([OH:30])=[CH:29][C:24]([O:23][CH2:22][CH2:21][CH2:20][O:19][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:36])[C:7]2[CH:6]=[C:5]([C:3]([O-:4])=[O:2])[CH:18]=[CH:17][C:16]=2[O:15]3)=[C:25]([CH2:34][CH3:35])[CH:26]=1)(=[O:33])[CH3:32].[C:31]([C:27]1[C:28]([OH:30])=[CH:29][C:24]([O:23][CH2:22][CH2:21][CH2:20][O:19][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:36])[C:7]2[CH:6]=[C:5]([C:3]([O-:4])=[O:2])[CH:18]=[CH:17][C:16]=2[O:15]3)=[C:25]([CH2:34][CH3:35])[CH:26]=1)(=[O:33])[CH3:32].[Na+:38].[Na+:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53870017HCID 53870017, compound

Product 1

HCID 131718522HCID 131718522, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 6-[3-(4-acetyl-2-ethyl-5-hydroxyphenoxy)propoxy]-9-oxo-9H-xanthene-2-carboxylic acid methyl ester (380 mg) and 5N aqueous sodium hydroxide solution (4 mL) in 1:1 methanol/tetrahydrofuran (20 mL) was stirred at room temperature for 24 hours. The mixture was acidified with aqueous 5N hydrochloric acid solution and the resulting precipitate was collected via vacuum filtration. This material was dissolved in a minimum of aqueous 1N sodium hydroxide solution and purified on MCI HP-20™ resin using a water/acetonitrile gradient. Lyophilization of the appropriate fractions provided 120 mg (35%) of the title product as a fluffy white solid: 1H-NMR (DMSO-d6) 8.64 (d, J=2 Hz, 1H), 8.27 (dd, J=9, 2 Hz, 1H), 8.05 (d, J=9 Hz, 1H), 7.59 (s, 1H), 7.44 (d, J=9 Hz, 1H), 7.13 (d, J= 2 Hz, 1H), 7.01 (dd, J=9, 2 Hz, 1H), 6.54 (s, 1H), 4.32 (t, J=5 Hz, 2H), 4.21 (t, J=6 Hz, 2H), 2.51 (m, 5H), 2.25 (quintet, J=5 Hz, 2H), 1.10 (t, J=8 Hz, 3H); MS-FAB (m/e) 521 (p+1, 35), 500 (22), 499 (63), 477 (18); IR (CHCl3, cm-1) 3450 (b), 2976, 1620, 1401, 1268, 1162, 1049. Anal. (C27H22O8Na2 . 1.5 H2O):

Workup

  1. filtrationthe resulting precipitate was collected via vacuum filtration
  2. dissolutionThis material was dissolved in a minimum of aqueous 1N sodium hydroxide solution
  3. custompurified on MCI HP-20™ resin

Sources & evidence

ORD record
ord-d55c4f382e2d4d89b02e2c6e19d00fc4
Source dataset
uspto-grants-1994_06
Patent number
US05324743

Reaction notes

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