Acetic Acid → HCID 178462545, compound

HRID 2354121Notes

Reaction equation

HRID 2354121 reaction equation
[C:1](O)(=O)[CH3:2].C(O[C:9](=O)[CH3:10])(=O)C.[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N+:20]1[C:28]2[C:23](=[CH:24][C:25]([S:29]([O-:32])(=[O:31])=[O:30])=[CH:26][CH:27]=2)[C:22]([CH3:41])([CH2:33][CH2:34][CH2:35][CH2:36][S:37]([OH:40])(=[O:39])=[O:38])[C:21]=1[CH3:42])([OH:14])=[O:13]>N1C=CC=CC=1>[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:28]2[C:23](=[CH:24][C:25]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:26][CH:27]=2)[C:22]([CH3:41])([CH2:33][CH2:34][CH2:35][CH2:36][S:37]([OH:40])(=[O:38])=[O:39])/[C:21]/1=[CH:42]\[CH:15]=[CH:16]\[CH:17]=[CH:18]\[C:19]1[C:9]([CH3:10])([CH2:33][CH2:34][CH2:35][CH2:36][S:37]([OH:40])(=[O:39])=[O:38])[C:27]2[C:28](=[CH:23][CH:24]=[C:25]([S:29]([O-:32])(=[O:31])=[O:30])[CH:26]=2)[N+:20]=1[CH2:1][CH3:2])([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 86614816HCID 86614816, compound

Product 1

HCID 178462545HCID 178462545, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[(1E,3E)-4-Anilinobuta-1,3-dienyl]-1-ethyl-3-methyl-3-(4-sulphobutyl) 3H-indolium-5-sulphonate (71 mg) was dissolved in a mixture of pyridine (45): acetic acid (45): acetic anhydride (10) (5 ml), at 90° C. To this solution was added crude 1-(5-carboxypentyl)-2,3-dimethyl-3-(4-sulphobutyl)-3H-indolium-5-sulphonate, portionwise at 20 minute intervals, until UV/Vis is analysis indicated complete conversion of half-dye components (λmax=524, 430 nm) to Cy5 dye product (λmax=653 nm). The solvent was then evaporated under vacuum and the residue purified by HPLC (RPC18. Water/methanol/triethylamine, then water/acetonitrile/TFA).

Workup

  1. customat 90° C
  2. customThe solvent was then evaporated under vacuum
  3. customthe residue purified by HPLC (RPC18

Sources & evidence

ORD record
ord-d09c99299ec94b4b96a452c9af819250
Source dataset
uspto-grants-2010_07
Patent number
US07750163B2

Reaction notes

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