Diethyl Ether → HCID 178496224, compound

HRID 339165

Reaction equation

HRID 339165 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N+:9]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:15][CH:16]=2)[C:11]([CH3:29])([CH2:22][CH2:23][CH2:24][S:25]([OH:28])(=[O:27])=[O:26])[C:10]=1/[CH:30]=[CH:31]/NC1C=CC=CC=1)([OH:3])=[O:2].[CH3:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][N+:46]1[C:54]2[C:49](=[CH:50][C:51]([S:55]([OH:58])(=[O:57])=[O:56])=[CH:52][CH:53]=2)[C:48]([CH3:66])([CH2:59][CH2:60][CH2:61][S:62]([OH:65])(=[O:64])=[O:63])[C:47]=1[CH3:67].C([O-])(=O)C.[Na+:72].C(OCC)C>C(O)(=O)C.C(OC(=O)C)(=O)C>[Na+:72].[Na+:72].[Na+:72].[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:15][CH:16]=2)[C:11]([CH3:29])([CH2:22][CH2:23][CH2:24][S:25]([OH:28])(=[O:26])=[O:27])/[C:10]/1=[CH:30]\[CH:31]=[CH:67]\[C:47]1[C:48]([CH3:66])([CH2:59][CH2:60][CH2:61][S:62]([OH:65])(=[O:64])=[O:63])[C:49]2[C:54](=[CH:53][CH:52]=[C:51]([S:55]([OH:58])(=[O:56])=[O:57])[CH:50]=2)[N+:46]=1[CH2:45][CH2:44][O:43][CH2:42][CH2:41][O:40][CH3:39])([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 885363471-(5-carboxypentyl)-3-methyl-2-((E)-2-phenylamino-vinyl)-5-sulfo-3-(3-sulfopropyl)-3H-indoliumHCID 885363611-[2-(2-methoxy-ethoxy)-ethyl]-2,3-dimethyl-5-sulfo-3-(3-sulfopropyl)-3H-indolium3×

Product 1

HCID 178496224HCID 178496224, compound

Reagents, catalysts & solvents 1

HCID 21895370AcOH AcOAcSolvent

Procedure

Both 1 mmol 1-(5-carboxypentyl)-3-methyl-2-((E)-2-phenylamino-vinyl)-5-sulfo-3-(3-sulfopropyl)-3H-indolium and 1 mmol 1-[2-(2-methoxy-ethoxy)-ethyl]-2,3-dimethyl-5-sulfo-3-(3-sulfo-propyl)-3H-indolium were dissolved in 20 ml acetic acid/acetic anhydride (1/1) followed by the addition of 200 mg sodium acetate. The solution was stirred under reflux for 15 min. After cooling to room temperature, 20 ml diethylether was added. The resulting precipitate (mixture of the diastereomers 550-1 compound 2 and 550-2 compound 2) was extracted by suction, washed with ether and dried.

Workup

  1. temperatureunder reflux for 15 min
  2. extractionwas extracted by suction
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-82c41909fbb3492d95201c071bc38bf3
Source dataset
uspto-grants-2014_11
Patent number
US08889884B1

Linked notes

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