Isopropanol → HCID 69017971, compound

HRID 1435569Notes

Reaction equation

HRID 1435569 reaction equation
[OH-].[Na+].[C:3]([CH2:6][N:7]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14][N:13]([CH2:19][C:20]([OH:22])=[O:21])[CH2:12][CH2:11][N:10]([CH2:23][C:24]([OH:26])=[O:25])[CH2:9][CH2:8]1)([OH:5])=[O:4].O1[CH2:29][CH:28]1[CH2:30][CH2:31][C:32]([OH:34])=[O:33].CC(O)C>O.C(O)CCC>[O:33]=[C:32]1[O:34][CH:28]([CH2:29][N:16]2[CH2:15][CH2:14][N:13]([CH2:19][C:20]([OH:22])=[O:21])[CH2:12][CH2:11][N:10]([CH2:23][C:24]([OH:26])=[O:25])[CH2:9][CH2:8][N:7]([CH2:6][C:3]([OH:5])=[O:4])[CH2:18][CH2:17]2)[CH2:30][CH2:31]1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecaneHCID 144751383-(Oxiran-2-yl)propanoic acid

Product 1

HCID 69017971HCID 69017971, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

8.3 g (207.6 mmol) of sodium hydroxide is added to 12.0 g (34.6 mmol) of 1,4,7-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane (D03A) in 50 ml of water. A solution that consists of 5.02 g (43.25 mmol) of 3-oxiranylpropionic acid (Dakoji et al., J. Am. Chem. Soc., 1996, 10971-10979) in 50 ml of n-butanol/50 ml of 2-propanol is added in drops thereto, and the solution is heated for 24 hours to 80° C. The reaction solution is evaporated to the dry state in a vacuum, the residue is mixed with 300 ml of water, and a pH of 3 is set with 3N hydrochloric acid. Then, it is extracted three times with 200 ml each of n-butanol, the combined butanol phases are evaporated to the dry state in a vacuum, and the residue is purified by chromatography (RP-18; mobile solvent: gradient that consists of water/acetonitrile).

Workup

  1. additionis added in drops
  2. temperaturethe solution is heated for 24 hours to 80° C
  3. customThe reaction solution is evaporated to the dry state in a vacuum
  4. additionthe residue is mixed with 300 ml of water
  5. extractionThen, it is extracted three times with 200 ml each of n-butanol
  6. customthe combined butanol phases are evaporated to the dry state in a vacuum
  7. customthe residue is purified by chromatography (RP-18; mobile solvent: gradient that consists of water/acetonitrile)

Sources & evidence

ORD record
ord-885a077e412a4125b2635262066581ce
Source dataset
uspto-grants-2009_11
Patent number
US07618957B2

Reaction notes

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