N-Hydroxysuccinimide → HCID 44622261, compound

HRID 876203Notes

Reaction equation

HRID 876203 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([O:16]C(C)(C)C)=[O:15].O[N:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28].Cl.C(N=C=NCCCN(C)C)C>FC(F)(F)C(O)=O.ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([O:16][N:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28])=[O:15]

Participants

6

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44622260HCID 44622260, compound

Product 1

HCID 44622261HCID 44622261, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 3-{2-[2-(2-Methoxyethoxy)ethoxy]ethoxy}propionate (131 mg, 0.45 mmol) was dissolved in trifluoroacetic acid and left at room temperature for 1 hour. The solvent was removed in vacuo and residual trifluoroacetic acid was removed by evaporation from dioxane. The deprotected intermediate was dissolved in dichloromethane and treated with N-hydroxysuccinimide (57 mg, 0.49 mmol) and ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (86 mg, 0.45 mmol) and stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed twice with water. The organic phase was dried over MgSO4 and concentrated in vacuo to provide 122 mg (82%).

Workup

  1. customThe solvent was removed in vacuo and residual trifluoroacetic acid
  2. customwas removed by evaporation from dioxane
  3. dissolutionThe deprotected intermediate was dissolved in dichloromethane
  4. washwashed twice with water
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto provide 122 mg (82%)

Sources & evidence

ORD record
ord-8c65e82aefd9445e917e0f2370d0f597
Source dataset
uspto-grants-2015_03
Patent number
US08987197B2

Reaction notes

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