Chloroform → HCID 18913796, compound

HRID 1084968Notes

Reaction equation

HRID 1084968 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:12]2[CH2:23][CH2:22][N:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20][CH2:19][N:18]([CH2:28][C:29]([OH:31])=[O:30])[CH2:17][CH2:16][N:15]([CH2:32][C:33]([OH:35])=[O:34])[CH2:14][CH2:13]2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C1N(CCO)CCN(C[CH2:46][S:47](O)(=O)=O)C1.C(Cl)(Cl)=S.C(Cl)(Cl)Cl>Cl>[N:1]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:12]2[CH2:13][CH2:14][N:15]([CH2:32][C:33]([OH:35])=[O:34])[CH2:16][CH2:17][N:18]([CH2:28][C:29]([OH:31])=[O:30])[CH2:19][CH2:20][N:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:22][CH2:23]2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1)=[C:46]=[S:47]

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 10040ThiophosgeneHCID 238314-(2-Hydroxyethyl)-1-piperazineethanesulfonic acidHCID 15297747HCID 15297747, compound

Product 1

HCID 18913796HCID 18913796, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of α-(4-aminophenyl)-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid, samarium-153 complex prepared from 220 μl of 153Sm solution in 0.1N HCl were added 2 μl of HEPES buffer (0.5M, pH 8.9), 2 μl of thiophosgen and 200 μl of chloroform. It was vortexed vigorously 2 or 3 times for a few seconds each time. The chloroform layer was discarded and the aqueous layer which contained mainly the desired product was saved and further purified. The yield of α-(4-isothiocyanatophenyl)-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid, samarium-153 complex, as analyzed by HPLC on GF-250 column based on the 153Sm activity using the HPLC System I was usually over 90%. To purify, the aqueous layer was passed through a Sep-Pak™ C-18 cartridge and eluted with 90 percent acetonitrile in water. The first 300 μl of effluent was discarded, and the desired product came off in the next 1200 μl, with 86-93% recovery. The bulk of the solvent was then evaporated off in a Speed Vac™ concentrator over a period of about 2 hours.

Workup

  1. customfor a few seconds

Sources & evidence

ORD record
ord-f2bb8edc94364559b162ca355b5ec768
Source dataset
uspto-grants-1991_04
Patent number
US05006643

Reaction notes

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