Chloroform → p-SCN-Benzyl-dtpa

HRID 62583Notes

Reaction equation

HRID 62583 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:27]([CH2:32][C:33]([OH:35])=[O:34])[CH2:28][C:29]([OH:31])=[O:30])[CH2:10][N:11]([CH2:16][CH2:17][N:18]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][C:20]([OH:22])=[O:21])[CH2:12][C:13]([OH:15])=[O:14])=[CH:4][CH:3]=1.[C:36](Cl)(Cl)=[S:37].C(Cl)(Cl)Cl>O>[C:33]([CH2:32][N:27]([CH2:28][C:29]([OH:31])=[O:30])[CH:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]=[C:36]=[S:37])=[CH:3][CH:4]=1)[CH2:10][N:11]([CH2:16][CH2:17][N:18]([CH2:19][C:20]([OH:22])=[O:21])[CH2:23][C:24]([OH:26])=[O:25])[CH2:12][C:13]([OH:15])=[O:14])([OH:35])=[O:34]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 10040ThiophosgeneHCID 1315962-[[3-(4-Aminophenyl)-2-[bis(carboxymethyl)amino]propyl]-[2-[bis(carboxymethyl)amino]ethyl]amino]acetic acid

Product 1

HCID 10143607p-SCN-Benzyl-dtpaYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6a (10 mg, 0.0155 mmol) in water (100 μL) was added dropwise 1M thiophosgene in CHCl3 (18.6 μL, 0.0186 mmol). The resulting mixture was stirred at room temperature for 3 h. The aqueous layer was concentrated in vacuo to provide pure 7a (10 mg, 99%) as a light yellowish solid. 1H NMR (MeOD, 300 MHz) δ 2.50-4.55 (m, 24H), 7.10-70 (m, 4H).

Workup

  1. concentrationThe aqueous layer was concentrated in vacuo

Sources & evidence

ORD record
ord-bc6d311a6d1e4d67abb1e9e44d62a533
Source dataset
uspto-grants-2016_09
Patent number
US09446995B2

Reaction notes

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