Dicyclohexylcarbodiimide → N-Succinimidyl 4-(tri-n-butylstannyl)benzoate

HRID 476547Notes

Reaction equation

HRID 476547 reaction equation
[CH2:1]([Sn:5]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:28][CH2:29][CH2:30][CH3:31])[C:6]1[CH:27]=[CH:26][C:9]([C:10]([O:12][Sn](CCCC)(CCCC)CCCC)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C1(N=C=NC2CCCCC2)CCCCC1.O[N:52]1[C:56](=[O:57])[CH2:55][CH2:54][C:53]1=[O:58]>C1COCC1.CC(O)=O>[CH3:35][CH2:34][CH2:33][CH2:32][Sn:5]([C:6]1[CH:27]=[CH:26][C:9]([C:10]([O:12][N:52]2[C:56](=[O:57])[CH2:55][CH2:54][C:53]2=[O:58])=[O:11])=[CH:8][CH:7]=1)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 16705680HCID 16705680, compound

Product 1

HCID 129957N-Succinimidyl 4-(tri-n-butylstannyl)benzoateYield 78.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.29 g (1.84 mmol) of tri-n-butylstannyl 4-(tri-n-butylstannyl)benzoate in 18.4 mL of anhydrous THF was added 417 mg (2.02 mmol) of dicyclohexylcarbodiimide (Sigma) and 212 mg (1.84 mmol) of N-hydroxysuccinimide (Sigma, and the mixture was stirred for 15 hours at room temperature. To the mixture was then added three drops of HOAc. The solids were removed by filtration, and the mixture was concentrated. Purification by silica gel chromatography (25% EtOAc/hexane) yielded 731 mg (78%) of N-succinimidyl 4-(tri-n-butylstannyl)benzoate: 1H NMR (CDCl3)δ 0.50-2.20 (m, 27H), 2.90 (s, 4H), 7.65 (d, J=8 Hz, 2H), 8.06 (d, J=8 Hz, 2H). IR (neat) 1780, 1750, 1190, 1055, 980 cm-1.

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe mixture was concentrated
  3. customPurification by silica gel chromatography (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-c2a48c97a4b543baae0dc2a8e1eae285
Source dataset
uspto-grants-1989_12
Patent number
US04885153

Reaction notes

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