Dicyclohexylcarbodiimide → HCID 20096977, compound

HRID 1769677Notes

Reaction equation

HRID 1769677 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[NH:24][C:25]([CH2:27][N:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]([OH:37])=[O:36])[CH2:30][CH2:29]1)=[O:26].[OH:38][CH:39]([C:50]1[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=1)[C:40]([C:42]1[CH:47]=[CH:46][C:45]([CH2:48][CH3:49])=[CH:44][CH:43]=1)=O.CN(C1C=CC=CN=1)C>CN(C)C=O.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH3:16])[C:18]=1[NH:24][C:25]([CH2:27][N:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]([O:37][CH:40]([C:42]2[CH:43]=[CH:44][C:45]([CH2:48][CH3:49])=[CH:46][CH:47]=2)[C:39](=[O:38])[C:50]2[CH:51]=[CH:52][C:53]([CH2:56][CH3:57])=[CH:54][CH:55]=2)=[O:36])[CH2:30][CH2:29]1)=[O:26]

Participants

8

Reactant 4

HCID 10868Dicyclohexylcarbodiimide2×HCID 218852-DimethylaminopyridineHCID 150442041,2-Bis(4-ethylphenyl)-2-hydroxyethanoneHCID 20096955HCID 20096955, compound

Product 1

HCID 20096977HCID 20096977, compoundYield 27.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,3-Dicyclohexylcarbodiimide (DCC; 0.81 g, 3.92 mmol) was added in one portion to a rapidly-stirred mixture of 4-[[[(2,6-dimethylphenyl)amino]carbonyl]methyl]-1-piperazineacetic acid (1.0 g, 3.27 mmol), 2-hydroxy-1,2-di-(4-ethylphenyl)ethanone (IX; 0.88 g, 3.27 mmol) and dimethylaminopyridine (DMAP: 40 mg) in anhydrous dimethylformamide (25 mL). After 2 hours at ambient temperature, an additional equivalent of DCC and DMAP were added. The mixture was stirred further for 22 hours at room temperature before it was heated to 70° C. for 6 hours. Upon cooling, the mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution and brine, dried and concentrated. Purification of the residue by flash chromatography on silica gel (gradient elution with 50% ethyl acetate in hexanes followed by ethyl acetate) afforded 0.50 g of the benzoin ester product (VI) as an off-white solid. The ester was used in subsequent reactions without additional purification.

Workup

  1. temperaturewas heated to 70° C. for 6 hours
  2. temperatureUpon cooling
  3. washwashed with saturated sodium bicarbonate solution and brine
  4. customdried
  5. concentrationconcentrated
  6. customPurification of the residue by flash chromatography on silica gel (gradient elution with 50% ethyl acetate in hexanes followed by ethyl acetate)

Sources & evidence

ORD record
ord-2b6067b4442849ffa4efd1ab5df8312c
Source dataset
uspto-grants-1995_01
Patent number
US05382584

Reaction notes

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