4-Toluenesulfonyl chloride → HCID 57816911, compound

HRID 1895857Notes

Reaction equation

HRID 1895857 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH:6]([NH2:17])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>C(N(CC)CC)C>[CH3:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([N:4]([CH2:5][CH:6]([NH:17][S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3][CH2:2][NH:1][S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 19853697HCID 19853697, compound

Product 1

HCID 57816911HCID 57816911, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Intermediate XXII is prepared based on the synthetic approach shown in Scheme 2. N1-(2-aminoethyl)-3-(4-nitrophenyl)propane-1,2-diamine (XX) is protected using tosyl chloride and triethylamine to afford tritosylated compound 4-methyl-N-(2-(4-methylphenylsulfonamido)-3-(4-nitrophenyl)propyl)-N-(2-(4-methylphenylsulfonamido)ethyl)benzenesulfonamide (XXI). Deprotonation of (XXI) with sodium ethoxide in ethanol produces a disodium salt of compound (XXI), compound (XXII). Compound (XX) is produced according to the method of Corson et al. (Corson, D. T.; Meares, C. F. Bioconjugate Chem. 2000, 11, 292-299, the disclosure of which is incorporated herein by reference).

Sources & evidence

ORD record
ord-f4bc3cf9b7a74eeb8da39e2a61110b13
Source dataset
uspto-grants-2013_08
Patent number
US08518715B2

Reaction notes

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