Dicyclohexylcarbodiimide → HCID 67694879, compound

HRID 725120Notes

Reaction equation

HRID 725120 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][C:24]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:35][C:25]=1[C:26]([NH:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:47]([NH:50][C:51]1[CH:60]=[CH:59][C:54]([O:55][CH2:56][CH2:57]O)=[CH:53][CH:52]=1)(=[O:49])[CH3:48]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:16]([O:23][C:24]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[CH:35][C:25]=1[C:26]([NH:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:57][CH2:56][O:55][C:54]1[CH:59]=[CH:60][C:51]([NH:50][C:47](=[O:49])[CH3:48])=[CH:52][CH:53]=1)=[O:33])=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 170834Acetamide, N-[4-(2-hydroxyethoxy)phenyl]-HCID 19711488HCID 19711488, compound

Product 1

HCID 67694879HCID 67694879, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.57 g (2.75 mmol) of dicyclohexylcarbodiimide was portionwise added to a solution of 1.05 g (2.5 mmol) of 4-{N-[2,5-di(benzyloxy)benzoyl]amino}butyric acid (compound of Example 1) in 16 ml of anhydrous methylene chloride at room temperature under stirring. After stirring the solution at the same temperature for 10 minutes 0.54 g (2.75 mmol) of 2-[4-(acetylamino)phenoxy]ethanol and 0.03 g (0.25 mmol) of 4-(N,N-dimethyl-amino)pyridine were added. The reaction mixture was stirred at room temperature for 4 hours, then diluted with methylene chloride and the solid product was filtered. The filtrate was successively washed with 5% acetic acid, 5% sodium hydrogen carbonate solution and water, then dried and evaporated under reduced pressure. The residue was separated by chromatography on a silica gel column by eluating with a 95:5 mixture of chloroform and methanol to obtain 0.82 g (55%) of the aimed product, m.p.: 141°-143° C.

Workup

  1. additionwere added
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. filtrationthe solid product was filtered
  4. washThe filtrate was successively washed with 5% acetic acid, 5% sodium hydrogen carbonate solution and water
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was separated by chromatography on a silica gel column
  8. additionby eluating with a 95:5 mixture of chloroform and methanol

Sources & evidence

ORD record
ord-c437e06d3f694fa18b631ecfb07d2cfb
Source dataset
uspto-grants-1998_01
Patent number
US05705529

Reaction notes

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