Tert-butyl 2-(2-(2-(2-hydroxybenzamido)ethyl)disulfanyl)ethylcarbamate → N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide

HRID 85401Notes

Reaction equation

HRID 85401 reaction equation
[OH:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][S:9][S:10][CH2:11][CH2:12][NH:13]C(=O)OC(C)(C)C)=[O:5]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:13][CH2:12][CH2:11][S:10][S:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:21]=[CH:22][CH:23]=[CH:24][C:2]=1[OH:1]

Participants

4

Reactant 1

HCID 86643520Tert-butyl 2-(2-(2-(2-hydroxybenzamido)ethyl)disulfanyl)ethylcarbamate

Product 1

HCID 58218979N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

tert-Butyl 2-(2-(2-(2-hydroxybenzamido)ethyl)disulfanyl)ethylcarbamate (400 mg, 1.08 mmol) was taken up in 25% TFA in CH2Cl2 (10 mL) and allowed to stand at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure to afford a quantitative yield of N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide as the TFA salt.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fda4b43a7e0c406db1d797fd0ffdf68c
Source dataset
uspto-grants-2014_09
Patent number
US08846972B2

Reaction notes

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