N-Hydroxysuccinimide → HCID 86746027, compound

HRID 1728539Notes

Reaction equation

HRID 1728539 reaction equation
C([CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1)(O)=O.Cl.C(N=C=NCCCN(C)C)C.O[N:29]1C(=O)C[CH2:31][C:30]1=[O:35].Cl.[CH3:37][S:38][S:39]CC[NH-].CSSCCN.Cl.CSSCCN>CN(C)C=O.O.C(N(CC)CC)C>[CH3:37][S:38][S:39][CH2:31][C:30]([NH:29][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1)=[O:35]

Participants

10

Reactant 6

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 19014054HCID 19014054, compound2×HCID 218327342-(Methyldisulfanyl)ethan-1-amineHCID 85609996131027-12-8HCID 86746028HCID 86746028, compound

Product 1

HCID 86746027HCID 86746027, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of m-(carboxymethoxy)phenyl acetone (6.1 g, 0.029 mmole) in N,N-dimethylformamide (56 ml, dried over molecular sieves, 3A) were added under nitrogen at 5° powdered 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 6.1 g, 0.032 mole) and N-hydroxysuccinimide (3.7 g, 0.032 mole). The resulting reaction mixture was then allowed to stir at 5° overnight. The complete formation of N-hydroxysuccinimic ester was observed. To the methyldithioethylamide hydrochloride (4.7 g, 0.029 mole, prepared in D above) in water (20-50 ml) was added triethylamine to adjust the pH to 8.5. Then the N-hydroxysuccinimic ester of m-(carboxymethoxy)phenyl acetone was added dropwise to the methyldithioethylamine solution with the adjustment of pH to 8.5, and the resulting solution was allowed to stir at 5° for 1 hour. Additional reagents, methyldithioethylamine hydrochloride (2 g, 0.0125 mole) and EDCI (3.0 g, 0.0156 mole), were added and the pH of the resulting solution was adjusted to 6.5 and the reaction mixture was allowed to stir at 5° overnight.

Workup

  1. customThe resulting reaction mixture
  2. stirringto stir at 5° for 1 hour
  3. stirringto stir at 5° overnight

Sources & evidence

ORD record
ord-122368b0ecb54adaad12abe425fc152b
Source dataset
uspto-grants-1994_07
Patent number
US05328828

Reaction notes

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