N-Hydroxysuccinimide → HCID 86757925, compound

HRID 840506Notes

Reaction equation

HRID 840506 reaction equation
[CH3:1][N:2]([CH3:28])[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]([OH:23])=[O:22])=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:24]=[CH:25][CH:26]=[CH:27][C:7]1=2.O[N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[O:36]=[C:31]1[CH2:32][CH2:33][C:34](=[O:35])[N:30]1[O:22][C:21](=[O:23])[CH2:20][CH2:19][CH2:18][O:17][C:15]1[CH:14]=[CH:13][C:12]2[CH:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:28])[C:7]3[CH:27]=[CH:26][CH:25]=[CH:24][C:8]=3[CH2:9][CH2:10][C:11]=2[CH:16]=1

Participants

5

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22619634HCID 22619634, compound

Product 1

HCID 86757925HCID 86757925, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 200 mg (0.52 mmol) of 8 in 40 ml of dichloromethane (distilled over calcium hydride) was added 92 mg (0.8 mmol) of N-hydroxysuccinimide and 152 mg (0.8 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC). The reaction mixture was allowed to stir at room temperature for 48 hours. The reaction mixture was diluted with 50 ml of dichloromethane and washed with 50 ml of brine, 2×50 ml of saturated sodium bicarbonate followed by 2×50 ml of brine. The resulting solution was dried (Na2SO4) and concentrated to give 245 mg (0.51 mmol, 98%) of 9 as a white solid.

Workup

  1. washwashed with 50 ml of brine, 2×50 ml of saturated sodium bicarbonate
  2. dry with materialThe resulting solution was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-99147295b79f4e90bbc77a2f98245b57
Source dataset
uspto-grants-2002_04
Patent number
US06368814B1

Reaction notes

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