Dicyclohexylcarbodiimide → HCID 54395470, compound

HRID 395721Notes

Reaction equation

HRID 395721 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20]([C:24]1[CH:50]=[CH:49][C:27]([C:28]([NH:30][C:31]2[CH:47]=[C:46]([NH2:48])[CH:45]=[CH:44][C:32]=2[C:33]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)=[O:34])=[O:29])=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21].C1(N=C=NC2CCCCC2)CCCCC1.C1C=NC2N(O)N=NC=2C=1>CN(C)C=O>[C:20]([C:24]1[CH:50]=[CH:49][C:27]([C:28]([NH:30][C:31]2[CH:47]=[C:46]([NH:48][C:17](=[O:19])[C@H:9]([CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:45]=[CH:44][C:32]=2[C:33]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)=[O:34])=[O:29])=[CH:26][CH:25]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 181649HOAtHCID 108118994-Amino-2-[[4-(1,1-dimethylethyl)benzoyl]amino]-N-(4-methoxyphenyl)benzamide

Product 1

HCID 54395470HCID 54395470, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-L-phenylalanine (130 mg, 0.49 mmol) in N,N-dimethylformamide (5 mL) cooled to 0° C. was added 2-(4-tert-butylbenzoylamino)-4-amino-N-(4-methoxyphenyl)benzamide (240 mg, 0.49 mmol), dicyclohexylcarbodiimide (112 mg, 0.54 mmol), and 7-aza-1-hydroxybenzotriazole (71 mg, 0.52 mmol). After stirring for 1 h, the reaction mixture was allowed to warm to room temperature. After 12 h, the mixture was filtered and the filtrate diluted with ethyl acetate. The solution was washed with 1 N aqueous sodium carbonate solution, 1.5 N aqueous citric acid solution, and water. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was chromatographed (silica gel, 10% ethyl acetate/90% methylene chloride) to give 195 mg (60%) of the title compound.

Workup

  1. waitAfter 12 h
  2. filtrationthe mixture was filtered
  3. additionthe filtrate diluted with ethyl acetate
  4. washThe solution was washed with 1 N aqueous sodium carbonate solution, 1.5 N aqueous citric acid solution, and water
  5. dry with materialThe organic layer was dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed (silica gel, 10% ethyl acetate/90% methylene chloride)

Sources & evidence

ORD record
ord-ec54b64801244991a03b92d1ccada771
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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