Dicyclohexylcarbodiimide → HCID 22842199, compound

HRID 1587195Notes

Reaction equation

HRID 1587195 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1.O.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1.C(N(CC)CC)C.C(Cl)(Cl)Cl.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([N:36]1[CH2:35][CH2:34][N:33]([C:30]2[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:32][CH:31]=2)[CH2:38][CH2:37]1)=[O:22])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

Product 1

HCID 22842199HCID 22842199, compoundYield 76.6%

Reagents, catalysts & solvents 4

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

9.00 g of N-(tert-butoxycarbonyl)-p-nitrophenylalanine was dissolved in 120 ml of tetrahydrofuran, 100 ml of methylene chloride and 100 ml of chloroform, and to the solution were sequentially added 7.68 g of N-(p-methoxyphenyl) piperazine dihydrochloride and 4.44 g of N-hydroxybenzotriazole monohydrate as well as 20 ml of triethylamine and 6 g of DCC, and the mixture was stirred at a room temperature for 18 hours. The reaction mixture was concentrated to one third of the original volume under a reduced pressure, and after adding 200 ml of 2.5% potassium carbonate aqueous solution, extracted twice with 200 ml of chloroform. The extract was dried over magnesium sulfate and concentrated under a reduced pressure to crystallize a product, which was washed with methanol to obtain 10.75 g of the title compound as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated to one third of the original volume under a reduced pressure
  2. additionafter adding 200 ml of 2.5% potassium carbonate aqueous solution
  3. extractionextracted twice with 200 ml of chloroform
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customto crystallize a product, which
  7. washwas washed with methanol

Sources & evidence

ORD record
ord-13aa0e2199d84032b92045ab7046ec31
Source dataset
uspto-grants-1993_06
Patent number
US05216150

Reaction notes

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