N-Hydroxysuccinimide → HCID 59510850, compound

HRID 1157067Notes

Reaction equation

HRID 1157067 reaction equation
[CH3:1][O:2][C:3]1[C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:16][CH3:17])[C:10]([O:18][CH3:19])=[C:9]2[C:4]=1[CH:5]1[CH2:20][CH:8]2[CH:7]=[CH:6]1.O[N:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28].Cl.CN(C)CCCN=C=NCC>ClCCl>[O:28]=[C:23]1[CH2:24][CH2:25][C:26](=[O:27])[N:22]1[O:14][C:13]([C:12]1[C:3]([O:2][CH3:1])=[C:4]2[C:9](=[C:10]([O:18][CH3:19])[C:11]=1[O:16][CH3:17])[CH:8]1[CH2:20][CH:5]2[CH:6]=[CH:7]1)=[O:15]

Participants

5

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59510866HCID 59510866, compound

Product 1

HCID 59510850HCID 59510850, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 15 (0.972 g, 3.52 mmol) in dichloromethane (80 mL) was added N-hydroxysuccinimide (0.547 g, 4.75 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.890 g, 4.64 mmol), and the resulting reaction mixture was stirred under dinitrogen for 15 h. The reaction mixture was diluted with dichloromethane (100 mL), washed twice with a 0.01 N HCl solution (50 mL), dried over sodium sulfate, and concentrated under reduced pressure. Purification was performed using silica gel chromatography (dichloromethane→2:1 ethyl acetate/hexanes) to yield 0.898 g (68%) of 3 as a colorless sticky solid. 1H NMR (300 MHz, CDCl3): δ=2.19-2.27 (m, 2H, CH—CH2—CH), 2.89 (bs, 4H, CH2—CH2), 3.86 (s, 3H, O—CH3), 3.92 (s, 3H, O—CH3), 3.95 (s, 3H, O—CH3), 4.19-4.23 (m, 2H, CH—CH(C)—CH2), 6.78-6.85 (m, 2H, HC═CH); 13C NMR (75 MHz, CDCl3): δ=25.9 (CH2—CH2), 47.7 (CH—CH(C)—CH2), 47.9 (CH—CH(C)—CH2), 61.7 (O—CH3), 62.3 (O—CH3), 62.6 (O—CH3), 68.6 (CH—CH2—CH), 137.7, 142.4 (CH═CH), 143.0 (CH═CH), 144.2, 147.9, 149.6, 149.9, 161.4, 169.1; TLC: Rf=0.42 (2:1 ethyl acetate/hexanes); ESI-MS calcd for C19H19NO7 [M+Na]+: 396.1059. found 396.1069.

Workup

  1. customthe resulting reaction mixture
  2. washwashed twice with a 0.01 N HCl solution (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-4251b0fdd86445aab9ca287156352ed4
Source dataset
uspto-grants-2010_10
Patent number
US07807140B2

Reaction notes

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