N-Hydroxysuccinimide → HCID 10232633, compound

HRID 840508Notes

Reaction equation

HRID 840508 reaction equation
[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][CH2:5][CH:6]1[C:12]2[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][C:21]([NH:23][CH2:24][C:25]3[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=3)=[O:22])=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:34]=[CH:35][CH:36]=[CH:37][C:7]1=2.O[N:40]1[C:44](=[O:45])[CH2:43][CH2:42][C:41]1=[O:46].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[O:46]=[C:41]1[CH2:42][CH2:43][C:44](=[O:45])[N:40]1[O:30][C:29](=[O:31])[C:28]1[CH:27]=[CH:26][C:25]([CH2:24][NH:23][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][O:17][C:15]2[CH:14]=[CH:13][C:12]3[CH:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:38])[C:7]4[CH:37]=[CH:36][CH:35]=[CH:34][C:8]=4[CH2:9][CH2:10][C:11]=3[CH:16]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22619641HCID 22619641, compound

Product 1

HCID 10232633HCID 10232633, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 87 mg (0.169 mmol) of the acid (15) in 10 ml of CH2Cl2 was treated with 40 mg (0.348 mmol) of N-hydroxysuccinimide and 87 mg (0.454 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl and stirred at room temperature overnight. The reaction was washed with H2O, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel using 10% ether in CH2Cl2 as eluent to give 34 mg (33%) of 16 as a white amorphous solid.

Workup

  1. washThe reaction was washed with H2O, saturated NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel using 10% ether in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-2195a4010a7f471e8645a3f3ca60a122
Source dataset
uspto-grants-2002_04
Patent number
US06368814B1

Reaction notes

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