N-Hydroxysuccinimide → HCID 59510880, compound

HRID 1157069Notes

Reaction equation

HRID 1157069 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:14])[N:5]([CH3:13])[C:6]([CH3:12])=[CH:7][C:8]=1[C:9]([OH:11])=[O:10].O[N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22].Cl.CN(C)CCCN=C=NCC>ClCCl>[O:22]=[C:17]1[CH2:18][CH2:19][C:20](=[O:21])[N:16]1[O:10][C:9]([C:8]1[CH:7]=[C:6]([CH3:12])[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[O:2][CH3:1])=[O:11]

Participants

5

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59510857HCID 59510857, compound

Product 1

HCID 59510880HCID 59510880, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5 (5.36 g, 27.2 mmol) in dichloromethane (500 mL) was added N-hydroxysuccinimide (4.23 g, 36.7 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (6.89 g, 35.9 mmol), and the resulting reaction mixture was stirred under dinitrogen for 15 h. The reaction mixture was washed twice with a 0.01 N HCl solution (150 mL), dried over sodium sulfate, and concentrated under reduced pressure. Purification was performed using silica gel chromatography (1:49 methanol/dichloromethane) to yield 7.83 g (98%) of 6 as a tan solid. 1H NMR (300 MHz, CDCl3): δ=2.31 (s, 3H, C—CH3), 4.08 (s, 4H, CH2), 3.50 (s, 3H, N—CH3), 3.98 (s, 3H, O—CH3), 6.29 (s, 1H, CH); 13C NMR (75 MHz, CDCl3): δ=20.6 (C—CH3), 25.8 (CH2), 32.0 (N—CH3), 60.8 (O—CH3), 103.0 (CH), 122.8, 140.7, 148.8, 159.9, 160.3, 169.0; TLC: Rf=0.33 (1:19 methanol/dichloromethane); ESI-MS calcd for C13H14N2O6 [M+H]+: 295.0930. found 295.0931.

Workup

  1. customthe resulting reaction mixture
  2. washThe reaction mixture was washed twice with a 0.01 N HCl solution (150 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-623dc8aa84aa409682f37a4fdc0f3c8c
Source dataset
uspto-grants-2010_10
Patent number
US07807140B2

Reaction notes

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