Chloroform → 2-({2-[Bis(carboxymethyl)amino]-5-(4-isothiocyanatophenyl)pentyl}({2-[bis(carboxy methyl)amino]ethyl})amino)acetic acid

HRID 62584Notes

Reaction equation

HRID 62584 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]([N:29]([CH2:34][C:35]([OH:37])=[O:36])[CH2:30][C:31]([OH:33])=[O:32])[CH2:12][N:13]([CH2:18][CH2:19][N:20]([CH2:25][C:26]([OH:28])=[O:27])[CH2:21][C:22]([OH:24])=[O:23])[CH2:14][C:15]([OH:17])=[O:16])=[CH:4][CH:3]=1.[C:38](Cl)(Cl)=[S:39].C(Cl)(Cl)Cl>O>[C:31]([CH2:30][N:29]([CH2:34][C:35]([OH:37])=[O:36])[CH:11]([CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]=[C:38]=[S:39])=[CH:3][CH:4]=1)[CH2:12][N:13]([CH2:18][CH2:19][N:20]([CH2:21][C:22]([OH:24])=[O:23])[CH2:25][C:26]([OH:28])=[O:27])[CH2:14][C:15]([OH:17])=[O:16])([OH:33])=[O:32]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 10040ThiophosgeneHCID 867026522-{[5-(4-Aminophenyl)-2-[bis(carboxymethyl)amino]pentyl] ({2-[bis(carboxymethyl)amino]ethyl})amino}acetic acid

Product 1

HCID 867026532-({2-[Bis(carboxymethyl)amino]-5-(4-isothiocyanatophenyl)pentyl}({2-[bis(carboxy methyl)amino]ethyl})amino)acetic acidYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6b (10.2 mg, 0.0152 mmol) in water (100 μL) was added dropwise 1M thiophosgene in CHCl3 (18.2 μL, 0.0182 mmol). The resulting mixture was stirred at room temperature for 3 h. The aqueous layer was concentrated in vacuo to provide pure 7b (10 mg, 97%) as a light yellowish solid. 1H NMR (MeOD, 300 MHz) δ 2.40-4.51 (m, 28H), 7.05-7.70 (m, 4H).

Workup

  1. concentrationThe aqueous layer was concentrated in vacuo

Sources & evidence

ORD record
ord-dbc4d8ea6fd245bc93bf3f71684eaa27
Source dataset
uspto-grants-2016_09
Patent number
US09446995B2

Reaction notes

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