Dicyclohexylcarbodiimide → HCID 86604821, compound

HRID 1297053Notes

Reaction equation

HRID 1297053 reaction equation
[CH2:1]([N:3]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]2[O:19][C:20]([CH:23]=[O:24])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]O)[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.[I:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[CH:43][CH:42]=1.CN(C1C=CC=CN=1)C>O1CCCC1>[CH2:1]([N:3]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]2[O:19][C:20]([CH:23]=[O:24])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:45](=[O:46])[C:44]1[CH:48]=[CH:49][C:41]([I:40])=[CH:42][CH:43]=1)[CH3:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 120854-Iodobenzoic acidHCID 218852-DimethylaminopyridineHCID 72377179HCID 72377179, compound

Product 1

HCID 86604821HCID 86604821, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 200 mL flask, 5 (7.63 g, 23.3 mmol), DCC (4.81 g, 23.3 mmol), 4-iodobenzoic acid (5.79 g, 23.3 mmol), and dimethylamino pyridine (0.85 g, 7.0 mmol) were dissolved in tetrahydrofuran (20 vol., 150 mL, freshly distilled from sodium and benzophenone) at room temperature and stirred overnight under Ar. The reaction mixture was filtered and the filtrate was added to a separatory funnel containing ether and water. The ether layer was rinsed several times with water, followed by dilute K2CO3, and then with dilute aqueous brine. The organic layer was evaporated onto silica gel and subsequently purified on silica gel with 3:1 hexane:ethyl acetate. Product 6A was a red viscous liquid (100% trans).

Workup

  1. distillationfreshly distilled from sodium and benzophenone) at room temperature
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate was added to a separatory funnel
  4. additioncontaining ether and water
  5. washThe ether layer was rinsed several times with water
  6. customThe organic layer was evaporated onto silica gel
  7. customsubsequently purified on silica gel with 3:1 hexane

Sources & evidence

ORD record
ord-640dc48e0ba24d988de27cdc4cd0c4a1
Source dataset
uspto-grants-2007_07
Patent number
US07250121B2

Reaction notes

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